U.S. patent application number 17/524184 was filed with the patent office on 2022-07-07 for organic light emitting device.
This patent application is currently assigned to LG DISPLAY CO., LTD.. The applicant listed for this patent is LG DISPLAY CO., LTD.. Invention is credited to Su-Na CHOI, Jeong-Dae SEO, In-Bum SONG.
Application Number | 20220216410 17/524184 |
Document ID | / |
Family ID | |
Filed Date | 2022-07-07 |
United States Patent
Application |
20220216410 |
Kind Code |
A1 |
CHOI; Su-Na ; et
al. |
July 7, 2022 |
ORGANIC LIGHT EMITTING DEVICE
Abstract
The present disclosure relates to an organic light emitting
device. In particular, the present disclosure relates to an organic
light emitting diode and an organic light emitting device each of
which includes at least one emitting material layer comprising a
boron-based dopant and an anthracene-based host substituted with at
least one deuterium, at least one electron blocking layer including
an amine-based compound substituted with at least one spiro aryl
group, and optionally at least one hole blocking layer including an
azine-based or a benzimidazole-based compound. The organic light
emitting diode and the organic light emitting device has improved
luminous efficiency and enhanced luminous lifespan.
Inventors: |
CHOI; Su-Na; (Paju-si,
KR) ; SONG; In-Bum; (Paju-si, KR) ; SEO;
Jeong-Dae; (Paju-si, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
LG DISPLAY CO., LTD. |
Seoul |
|
KR |
|
|
Assignee: |
LG DISPLAY CO., LTD.
Seoul
KR
|
Appl. No.: |
17/524184 |
Filed: |
November 11, 2021 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C07C 15/28 20060101 C07C015/28; C07F 5/02 20060101
C07F005/02; C09K 11/06 20060101 C09K011/06; C07D 307/91 20060101
C07D307/91 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 28, 2020 |
KR |
10-2020-0184940 |
Claims
1. An organic light emitting device, comprising: a substrate; and
an organic light emitting diode over the substrate, the organic
light emitting diode including a first electrode, a second
electrode facing the first electrode and an emissive layer disposed
between the first electrode and the second electrode, wherein the
emissive layer comprises a first emitting material layer including
a first dopant and a first host and a first electron blocking layer
disposed between the first electrode and the first emitting
material layer, wherein the first dopant includes a boron-based
compound having the following structure of Formula 1A or Formula
1B, wherein the first host includes an anthracene-based compound
having the following structure of Formula 3, and wherein the first
electron blocking layer includes an amine-based compound having the
following structure of Formula 5: ##STR00071## wherein each of
R.sub.11 to R.sub.14 and each of R.sub.21 to R.sub.24 is
independently selected from the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group, a C.sub.6-C.sub.30 aryl group, a
C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30 hetero aryl
group and a C.sub.3-C.sub.30 alicyclic group, or adjacent two of
R.sub.11 to R.sub.14 and R.sub.21 to R.sub.24 form a fused ring,
wherein each of the aryl group, the aryl amino group, the hetero
aryl group and the alicyclic group of R.sub.11 to R.sub.14 and
R.sub.21 to R.sub.24 is independently unsubstituted or substituted
with at least one C.sub.1-C.sub.10 alkyl group; each of R.sub.31
and R.sub.41 is independently selected from the group consisting of
hydrogen, a C.sub.1-C.sub.10 alkyl group, a C.sub.6-C.sub.30 aryl
group, a C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30
hetero aryl group and a C.sub.3-C.sub.30 alicyclic group, wherein
each of the aryl group, the aryl amino group, the hetero aryl group
and the alicyclic group of R.sub.31 and R.sub.41 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; R.sub.51 is selected form the group consisting of
hydrogen, a C.sub.1-C.sub.10 alkyl group, a C.sub.3-C.sub.15 cyclo
alkyl group, a C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl
amino group, a C.sub.5-C.sub.30 hetero aryl group. a
C.sub.3-C.sub.30 alicyclic group and a C.sub.5-C.sub.30 hetero
cyclic group, wherein each of the cyclo alkyl group, the aryl
group, the aryl amino group, the hetero aryl group, the alicyclic
group and the hetero cyclic group of R.sub.51 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; when each of R.sub.31, R.sub.41 and R.sub.51 is a
C.sub.6-C.sub.30 aryl group substituted with at least one
C.sub.1-C.sub.10 alkyl group, the substituted alkyl group is linked
to each other to form a fused ring; ##STR00072## wherein X is
NR.sub.1, CR.sub.2R.sub.3, O, S, Se or SiR.sub.4R.sub.5, each of
R.sub.1 to R.sub.5 is independently selected from the group
consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.6-C.sub.30 aryl group, a C.sub.5-C.sub.30 hetero aryl group
and a C.sub.3-C.sub.30 alicyclic group; each of R.sub.61 to
R.sub.64 is independently selected from the group consisting of
hydrogen, a C.sub.1-C.sub.10 alkyl group, a C.sub.6-C.sub.30 aryl
group, a C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30
hetero aryl group and a C.sub.3-C.sub.30 alicyclic group, or
adjacent two of R.sub.61 to R.sub.64 form a fused ring, wherein
each of the aryl group, the aryl amino group, the hetero aryl group
and the alicyclic group of R.sub.61 to R.sub.64 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; each of R.sub.71 to R.sub.74 is independently selected
from the group consisting of hydrogen, a C.sub.1-C.sub.10 alkyl
group and a C.sub.3-C.sub.30 alicyclic group; R.sub.81 is selected
from the group consisting of a C.sub.6-C.sub.30 aryl group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group, or R.sub.81 and R.sub.61 form a fused ring, wherein each of
the aryl group, the hetero aryl group and the alicyclic group of
R.sub.81 is independently unsubstituted or substituted with at
least one C.sub.1-C.sub.10 alkyl group; R.sub.82 is selected from
the group consisting of a C.sub.6-C.sub.30 aryl group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group, wherein each of the aryl group, the hetero aryl group and
the alicyclic group of R.sub.82 is independently unsubstituted or
substituted with at least one C.sub.1-C.sub.10 alkyl group;
R.sub.91 is selected from the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group, a C.sub.3-C.sub.15 cyclo alkyl group,
a C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group,
a C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30
alicyclic group, wherein each of the cyclo alkyl group, the aryl
group, the aryl amino group, the hetero aryl group and the
alicyclic group of R.sub.91 is independently unsubstituted or
substituted with at least one C.sub.1-C.sub.10 alkyl group; when
each of R.sub.81, R.sub.82 and R.sub.91 is a C.sub.6-C.sub.30 aryl
group substituted with at least one C.sub.1-C.sub.10 alkyl group,
the substituted alkyl group is linked to each other to form a fused
ring; ##STR00073## wherein each of Ar1 and Ar2 is independently a
C.sub.6-C.sub.30 aryl group or a C.sub.5-C.sub.30 hetero aryl
group; L is a single bond, a C.sub.6-C.sub.20 arylene group or a
C.sub.5-C.sub.20 hetero arylene group; a is an integer of 0 to 8;
each of b, c and d is independently an integer of 0 to 30, wherein
at least one of a, b, c and d is a positive integer; ##STR00074##
wherein L.sub.3 is C.sub.6-C.sub.30 arylene; o is 0 or 1; each of
R.sub.121 and R.sub.122 is independently C.sub.6-C.sub.30 aryl or
C.sub.5-C.sub.30 hetero aryl, wherein each of the C.sub.6-C.sub.30
aryl and the C.sub.5-C.sub.30 hetero aryl is independently
unsubstituted or substituted with at least one of C.sub.1-C.sub.10
alkyl and C.sub.6-C.sub.30 aryl.
2. The organic light emitting device of claim 1, wherein each of
R.sub.11 to R.sub.14, R.sub.21 to R.sub.24, R.sub.31 and R.sub.41
in Formula 1A is independently selected from the group consisting
of hydrogen, a C.sub.1-C.sub.10 alkyl group, a C.sub.6-C.sub.30
aryl group and a C.sub.5-C.sub.30 hetero aryl group, wherein each
of the aryl group and the hetero aryl group of R.sub.11 to
R.sub.14, R.sub.21 to R.sub.24, R.sub.31 and R.sub.41 is
independently unsubstituted or substituted with a C.sub.1-C.sub.10
alkyl group, wherein R.sub.51 in Formula 1A is selected from the
group consisting of C.sub.1-C.sub.10 alkyl group, a
C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30 hetero aryl
group and a C.sub.3-C.sub.30 hetero cyclic group, and wherein each
of the hetero aryl group, the aryl amino group and the hetero
cyclic group of R.sub.51 is independently unsubstituted or
substituted with a C.sub.1-C.sub.10 alkyl group.
3. The organic light emitting device of claim 1, wherein X in
Formula 1B is O or S, wherein each of R.sub.61 to R.sub.64 in
Formula 1B is independently selected from the group consisting of
hydrogen, a C.sub.1-C.sub.10 alkyl group and a C.sub.6-C.sub.30
aryl amino group, or adjacent two of R.sub.61 to R.sub.64 form a
fused ring, wherein each of R.sub.71 to R.sub.74 is independently
selected from the group consisting of hydrogen and a
C.sub.1-C.sub.10 alkyl group, wherein R.sub.81 is selected from the
group consisting of a C.sub.6-C.sub.30 aryl group and a
C.sub.5-C.sub.30 hetero aryl group, or R.sub.81 and R.sub.61 form a
fused ring, wherein each of the aryl group and the hetero aryl
group of R.sub.81 is independently unsubstituted or substituted
with a C.sub.1-C.sub.10 alkyl group, wherein R.sub.82 is selected
from the group consisting of a C.sub.6-C.sub.30 aryl group and a
C.sub.5-C.sub.30 hetero aryl group, wherein each of the aryl group
and the hetero aryl group of R.sub.82 is independently
unsubstituted or substituted with a C.sub.1-C.sub.10 alkyl group,
and wherein R.sub.91 is a C.sub.1-C.sub.10 alkyl group.
4. The organic light emitting device of claim 1, wherein the first
dopant is selected from the following boron-based compounds:
##STR00075## ##STR00076## ##STR00077##
5. The organic light emitting device of claim 1, wherein the first
host is selected from the following anthracene-based compounds.
##STR00078## ##STR00079##
6. The organic light emitting device of claim 1, wherein the
amine-based compound is selected from the following amine-based
compounds: ##STR00080## ##STR00081## ##STR00082## ##STR00083##
##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088##
##STR00089##
7. The organic light emitting device of claim 1, wherein the
emissive layer further comprises a first hole blocking layer
disposed between the first emitting material layer and the second
electrode.
8. The organic light emitting device of claim 7, wherein the first
hole blocking layer includes at least one of an azine-based
compound having the following structure of Formula 7 and a
benzimidazole-based compound having the following structure of
Formula 9: ##STR00090## wherein each of Y.sub.1 to Y.sub.5 is
independently CR.sub.131 or N, one to three of Y.sub.1 to Y.sub.5
is N, and R.sub.131 is a C.sub.6-C.sub.30 aryl group; L is a
C.sub.6-C.sub.30 arylene group; R.sub.132 is a C.sub.6-C.sub.30
aryl group or a C.sub.5-C.sub.30 hetero aryl group, wherein the
C.sub.6-C.sub.30 aryl group is independently unsubstituted or
substituted with another C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30
hetero aryl or forms a spiro structure with a C.sub.10-C.sub.30
fused aryl ring or a C.sub.10-C.sub.30 fused hetero aryl ring,
wherein the another C.sub.6-C.sub.30 aryl is independently
unsubstituted or further substituted with other C.sub.6-C.sub.30
aryl or C.sub.5-C.sub.30 hetero aryl or forms a spiro structure
with a C.sub.10-C.sub.30 fused aryl ring; R.sub.133 is hydrogen or
adjacent two of R.sub.133 form a fused aromatic ring; r is 0 or 1;
s is 1 or 2; and t is an integer of 0 to 4; ##STR00091## wherein Ar
is C.sub.10-C.sub.30 arylene; R.sub.141 is a C.sub.6-C.sub.30 aryl
group or a C.sub.5-C.sub.30 hetero aryl group, each of the
C.sub.6-C.sub.30 aryl group and the C.sub.5-C.sub.30 hetero aryl
group is independently unsubstituted or substituted with
C.sub.1-C.sub.10 alkyl; and each of R.sub.142 and R.sub.143 is
independently hydrogen, a C.sub.1-C.sub.10 alkyl group or a
C.sub.6-C.sub.30 aryl group.
9. The organic light emitting device of claim 8, wherein the
azine-based compound is selected from the following azine-based
compounds: ##STR00092## ##STR00093## ##STR00094## ##STR00095##
##STR00096## ##STR00097## ##STR00098## ##STR00099##
10. The organic light emitting device of claim 8, wherein the
benzimidazole-based compound is selected from the following
benzimidazole-based compounds: ##STR00100##
11. The organic light emitting device of claim 1, wherein the
emissive layer further comprises a second emitting material layer
disposed between the first emitting material layer and the second
electrode and a first charge generation layer disposed between the
first and second emitting material layers.
12. The organic light emitting device of claim 1, wherein the
second emitting material layer includes a second dopant and a
second host, wherein the second dopant includes the boron-based
compound having the structure of Formula 1A or Formula 1B, and
wherein the second host includes the anthracene-based compound
having the structure of Formula 3.
13. The organic light emitting device of claim 1, wherein the
emissive layer further comprises a second electron blocking layer
disposed between the first charge generation layer and the second
emitting material layer, and wherein the second electron blocking
layer includes the amine-based compound having the structure of
Formula 5.
14. The organic light emitting device of claim 11, wherein the
emissive layer further comprises at least one of a first hole
blocking layer disposed between the first emitting material layer
and the first charge generation layer and a second hole blocking
layer disposed between the second emitting material layer and the
second electrode.
15. The organic light emitting device of claim 11, wherein the
emissive layer further comprises a third emitting material layer
disposed between the second emitting material layer and the second
electrode and a second charge generation layer disposed between the
second and third emitting material layers.
16. The organic light emitting device of claim 1, wherein the
substrate defines a red pixel region, a green pixel region and a
blue pixel region and the organic light emitting diode is located
correspondingly to the red pixel region, the green pixel region and
the blue pixel region, and the organic light emitting device
further comprises a color conversion layer disposed between the
substrate and the organic light emitting diode or over the organic
light emitting diode correspondingly to the red pixel region and
the green pixel region.
17. The organic light emitting device of claim 11, wherein the
second emitting material layer emits yellow-green light or
red-green light.
18. The organic light emitting device of claim 15, wherein the
second emitting material layer emits yellow-green light or
red-green light.
19. The organic light emitting device of claim 17, wherein the
substrate defines a red pixel region, a green pixel region and a
blue pixel region and the organic light emitting diode is located
correspondingly to the red pixel region, the green pixel region and
the blue pixel region, and the organic light emitting device
further comprises a color filter layer disposed between the
substrate and the organic light emitting diode or over the organic
light emitting diode correspondingly to the red pixel region, the
green pixel region and the blue pixel region.
20. The organic light emitting device of claim 18, wherein the
substrate defines a red pixel region, a green pixel region and a
blue pixel region and the organic light emitting diode is located
correspondingly to the red pixel region, the green pixel region and
the blue pixel region, and the organic light emitting device
further comprises a color conversion layer disposed between the
substrate and the organic light emitting diode or over the organic
light emitting diode correspondingly to the red pixel region and
the green pixel region.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims the priority benefit under 35 U.S.C.
.sctn. 119(a) of Korean Patent Application No. 10-2020-0184940
filed in the Republic of Korea on Dec. 28, 2020, the entire
contents of which are expressly incorporated herein by reference in
its entirety into the present application.
BACKGROUND
Technical Field
[0002] The present disclosure relates to an organic light emitting
device, and more specifically, to an organic light emitting device
having excellent luminous efficiency and luminous lifespan.
Discussion of the Related Art
[0003] An organic light emitting diode (OLED) among a flat display
device used widely has come into the spotlight as a display device
replacing rapidly a liquid crystal display device (LCD). The OLED
can be formed as a thin organic film less than 2000 .ANG. and can
implement unidirectional or bidirectional images by electrode
configurations. Also, the OLED can be formed even on a flexible
transparent substrate such as a plastic substrate so that a
flexible or a foldable display device can be realized with ease
using the OLED. In addition, the OLED can be driven at a lower
voltage and the OLED has excellent high color purity compared to
the LCD.
[0004] Since fluorescent material uses only singlet exciton energy
in the luminous process, the related art fluorescent material shows
low luminous efficiency. On the contrary, phosphorescent material
can show high luminous efficiency since it uses triplet exciton
energy as well as singlet exciton energy in the luminous process.
However, metal complex, representative phosphorescent material, has
short luminous lifespan for commercial use. Particularly, blue
luminous materials have not showed satisfactory luminous efficiency
and luminous lifespan compared to other color luminous materials.
Therefore, there is a need to develop a new compound or a device
structure that can enhance luminous efficiency and luminous
lifespan of the organic light emitting diode.
SUMMARY
[0005] Accordingly, embodiments of the present disclosure are
directed to an organic light emitting device that substantially
obviates one or more of the problems due to the limitations and
disadvantages of the related art.
[0006] An aspect of the present disclosure is to provide an organic
light emitting device with improved luminous efficiency and
luminous lifespan.
[0007] Additional features and aspects will be set forth in the
description that follows, and in part will be apparent from the
description, or can be learned by practice of the inventive
concepts provided herein. Other features and aspects of the
inventive concept can be realized and attained by the structure
particularly pointed out in the written description, or derivable
therefrom, and the claims hereof as well as the appended
drawings.
[0008] To achieve these and other aspects of the inventive
concepts, as embodied and broadly described herein, an organic
light emitting device comprises a substrate; and an organic light
emitting diode over the substrate, the organic light emitting diode
including a first electrode, a second electrode facing the first
electrode and an emissive layer disposed between the first
electrode and the second electrode, wherein the emissive layer
comprises a first emitting material layer including a first dopant
and a first host and a first electron blocking layer disposed
between the first electrode and the first emitting material layer,
wherein the first dopant includes a boron-based compound having the
following structure of Formula 1A or Formula 1B, wherein the first
host includes an anthracene-based compound having the following
structure of Formula 3, and wherein the first electron blocking
layer includes an amine-based compound having the following
structure of Formula 5:
##STR00001## [0009] wherein each of R.sub.11 to R.sub.14 and each
of R.sub.21 to R.sub.24 is independently selected from the group
consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group, or adjacent two of R.sub.11 to R.sub.14 and R.sub.21 to
R.sub.24 form a fused ring, wherein each of the aryl group, the
aryl amino group, the hetero aryl group and the alicyclic group of
R.sub.11 to R.sub.14 and R.sub.21 to R.sub.24 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; each of R.sub.31 and R.sub.41 is independently
selected from the group consisting of hydrogen, a C.sub.1-C.sub.10
alkyl group, a C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl
amino group, a C.sub.5-C.sub.30 hetero aryl group and a
C.sub.3-C.sub.30 alicyclic group, wherein each of the aryl group,
the aryl amino group, the hetero aryl group and the alicyclic group
of R.sub.31 and R.sub.41 is independently unsubstituted or
substituted with at least one C.sub.1-C.sub.10 alkyl group;
R.sub.51 is selected form the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group, a C.sub.3-C.sub.15 cyclo alkyl group,
a C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group,
a C.sub.5-C.sub.30 hetero aryl group. a C.sub.3-C.sub.30 alicyclic
group and a C.sub.5-C.sub.30 hetero cyclic group, wherein each of
the cyclo alkyl group, the aryl group, the aryl amino group, the
hetero aryl group, the alicyclic group and the hetero cyclic group
of R.sub.51 is independently unsubstituted or substituted with at
least one C.sub.1-C.sub.10 alkyl group; when each of R.sub.31,
R.sub.41 and R.sub.51 is a C.sub.6-C.sub.30 aryl group substituted
with at least one C.sub.1-C.sub.10 alkyl group, the substituted
alkyl group is linked to each other to form a fused ring;
[0009] ##STR00002## [0010] wherein X is NR.sub.1, CR.sub.2R.sub.3,
O, S, Se or SiR.sub.4R.sub.5, each of R.sub.1 to R.sub.5 is
independently selected from the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group, a C.sub.6-C.sub.30 aryl group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group; each of R.sub.61 to R.sub.64 is independently selected from
the group consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group, or adjacent two of R.sub.61 to R.sub.64 form a fused ring,
wherein each of the aryl group, the aryl amino group, the hetero
aryl group and the alicyclic group of R.sub.61 to R.sub.64 is
independently unsubstituted or substituted with at least one
C.sub.1-C.sub.10 alkyl group; each of R.sub.71 to R.sub.74 is
independently selected from the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group and a C.sub.3-C.sub.30 alicyclic
group; R.sub.81 is selected from the group consisting of a
C.sub.6-C.sub.30 aryl group, a C.sub.5-C.sub.30 hetero aryl group
and a C.sub.3-C.sub.30 alicyclic group, or R.sub.81 and R.sub.61
form a fused ring, wherein each of the aryl group, the hetero aryl
group and the alicyclic group of R.sub.81 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; R.sub.82 is selected from the group consisting of a
C.sub.6-C.sub.30 aryl group, a C.sub.5-C.sub.30 hetero aryl group
and a C.sub.3-C.sub.30 alicyclic group, wherein each of the aryl
group, the hetero aryl group and the alicyclic group of R.sub.82 is
independently unsubstituted or substituted with at least one
C.sub.1-C.sub.10 alkyl group; R.sub.91 is selected from the group
consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.3-C.sub.15 cyclo alkyl group, a C.sub.6-C.sub.30 aryl group,
a C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30 hetero aryl
group and a C.sub.3-C.sub.30 alicyclic group, wherein each of the
cyclo alkyl group, the aryl group, the aryl amino group, the hetero
aryl group and the alicyclic group of R.sub.91 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; when each of R.sub.81, R.sub.82 and R.sub.91 is a
C.sub.6-C.sub.30 aryl group substituted with at least one
C.sub.1-C.sub.10 alkyl group, the substituted alkyl group is linked
to each other to form a fused ring;
[0010] ##STR00003## [0011] wherein each of Ar1 and Ar2 is
independently a C.sub.6-C.sub.30 aryl group or a C.sub.5-C.sub.30
hetero aryl group; L is a single bond, a C.sub.6-C.sub.20 arylene
group or a C.sub.5-C.sub.20 hetero arylene group; a is an integer
of 0 to 8; each of b, c and d is independently an integer of 0 to
30, wherein at least one of a, b, c and d is a positive
integer;
[0011] ##STR00004## [0012] wherein L.sub.3 is C.sub.6-C.sub.30
arylene; o is 0 or 1; each of R.sub.121 and R.sub.122 is
independently C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30 hetero
aryl, wherein each of the C.sub.6-C.sub.30 aryl and the
C.sub.5-C.sub.30 hetero aryl is optionally substituted with at
least one of C.sub.1-C.sub.10 alkyl and C.sub.6-C.sub.30 aryl,
respectively.
[0013] As an example, each of R.sub.11 to R.sub.14, R.sub.21 to
R.sub.24, R.sub.31 and R.sub.41 in Formula 1A may be independently
selected from the group consisting of hydrogen, a C.sub.1-C.sub.10
alkyl group, a C.sub.6-C.sub.30 aryl group and a C.sub.5-C.sub.30
hetero aryl group, wherein each of the aryl group and the hetero
aryl group of R.sub.11 to R.sub.14, R.sub.21 to R.sub.24, R.sub.31
and R.sub.41 may be independently unsubstituted or substituted with
a C.sub.1-C.sub.10 alkyl group, wherein R.sub.51 in Formula 1A may
be selected from the group consisting of C.sub.1-C.sub.10 alkyl
group, a C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30
hetero aryl group and a C.sub.3-C.sub.30 hetero cyclic group, and
wherein each of the hetero aryl group, the aryl amino group and the
hetero cyclic group of R.sub.51 may be independently unsubstituted
or substituted with a C.sub.1-C.sub.10 alkyl group.
[0014] Alternatively, X in Formula 1B may be O or S, wherein each
of R.sub.61 to R.sub.64 in Formula 1B may be independently selected
from the group consisting of hydrogen, a C.sub.1-C.sub.10 alkyl
group and a C.sub.6-C.sub.30 aryl amino group, or adjacent two of
R.sub.61 to R.sub.64 may form fused ring, wherein each of R.sub.71
to R.sub.74 may be independently selected from the group consisting
of hydrogen and a C.sub.1-C.sub.10 alkyl group, wherein R.sub.81
may be selected from the group consisting of a C.sub.6-C.sub.30
aryl group and a C.sub.5-C.sub.30 hetero aryl group, or R.sub.81
and R.sub.61 may form a fused ring, wherein each of the aryl group
and the hetero aryl group of R.sub.81 may be independently
unsubstituted or substituted with a C.sub.1-C.sub.10 alkyl group,
wherein R.sub.82 may be selected from the group consisting of a
C.sub.6-C.sub.30 aryl group and a C.sub.5-C.sub.30 hetero aryl
group, wherein each of the aryl group and the hetero aryl group of
R.sub.82 may be independently unsubstituted or substituted with a
C.sub.1-C.sub.10 alkyl group, and wherein R.sub.91 may be a
C.sub.1-C.sub.10 alkyl group.
[0015] The emissive layer may further comprise a first hole
blocking layer disposed between the first emitting material layer
and the second electrode.
[0016] As an example, the first hole blocking layer may comprise at
least one of an azine-based compound having the following structure
of Formula 7 and a benzimidazole-based compound having the
following structure of Formula 9:
##STR00005## [0017] wherein each of Y.sub.1 to Y.sub.5 is
independently CR.sub.131 or N, one to three of Y.sub.1 to Y.sub.5
is N, and R.sub.131 is a C.sub.6-C.sub.30 aryl group; L is a
C.sub.6-C.sub.30 arylene group; R.sub.132 is a C.sub.6-C.sub.30
aryl group or a C.sub.5-C.sub.30 hetero aryl group, wherein the
C.sub.6-C.sub.30 aryl group is optionally substituted with another
C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30 hetero aryl or forms a
spiro structure with a C.sub.10-C.sub.30 fused aryl ring or a
C.sub.10-C.sub.30 fused hetero aryl ring, wherein the another
C.sub.6-C.sub.30 aryl is optionally further substituted with other
C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30 hetero aryl or forms a
spiro structure with a C.sub.10-C.sub.30 fused aryl ring; R.sub.133
is hydrogen or adjacent two of R.sub.133 form a fused aromatic
ring; r is 0 or 1; s is 1 or 2; and t is an integer of 0 to 4;
[0017] ##STR00006## [0018] wherein Ar is C.sub.10-C.sub.30 arylene;
R.sub.141 is a C.sub.6-C.sub.30 aryl group or a C.sub.5-C.sub.30
hetero aryl group, each of the C.sub.6-C.sub.30 aryl group and the
C.sub.5-C.sub.30 hetero aryl group is optionally substituted with
C.sub.1-C.sub.10 alkyl; and each of R.sub.142 and R.sub.143 is
independently hydrogen, a C.sub.1-C.sub.10 alkyl group or a
C.sub.6-C.sub.30 aryl group.
[0019] Alternatively, the emissive layer may further comprise a
second emitting material layer disposed between the first emitting
material layer and the second electrode and a first charge
generation layer disposed between the first and second emitting
material layers.
[0020] The second emitting material layer may include a second
dopant and a second host, wherein the second dopant may include the
boron-based compound having the structure of Formula 1A or Formula
1B, and wherein the second host may include the anthracene-based
compound having the structure of Formula 3.
[0021] In addition, the emissive layer may further comprise a
second electron blocking layer disposed between the first charge
generation layer and the second emitting material layer, and
wherein the second electron blocking layer may include the
amine-based compound having the structure of Formula 5.
[0022] The emissive layer may further comprise at least one of a
first hole blocking layer disposed between the first emitting
material layer and the first charge generation layer and a second
hole blocking layer disposed between the second emitting material
layer and the second electrode.
[0023] For example, the emissive layer may further comprise a third
emitting material layer disposed between the second emitting
material layer and the second electrode and a second charge
generation layer disposed between the second and third emitting
material layers.
[0024] The substrate may define a red pixel region, a green pixel
region and a blue pixel region and the organic light emitting diode
may be located correspondingly to the red pixel region, the green
pixel region and the blue pixel region, and the organic light
emitting device may further comprise a color conversion layer
disposed between the substrate and the organic light emitting diode
or over the organic light emitting diode correspondingly to the red
pixel region and the green pixel region.
[0025] In one exemplary aspect, the second emitting material layer
may emit yellow-green (YG) light or red-green (RG) light.
[0026] In this case, the substrate may define a red pixel region, a
green pixel region and a blue pixel region and the organic light
emitting diode may be located correspondingly to the red pixel
region, the green pixel region and the blue pixel region, and the
organic light emitting device may further comprise a color filter
layer disposed between the substrate and the organic light emitting
diode or over the organic light emitting diode correspondingly to
the red pixel region, the green pixel region and the blue pixel
region.
[0027] It is to be understood that both the foregoing general
description and the following detailed description are exemplary
and explanatory and are intended to provide further explanation of
the inventive concepts as claimed.
BRIEF DESCRIPTION OF THE DRAWINGS
[0028] The accompanying drawings, which are included to provide a
further understanding of the disclosure, are incorporated in and
constitute a part of this application, illustrate embodiments of
the disclosure and together with the description serve to explain
various principles of the disclosure.
[0029] FIG. 1 is a schematic circuit diagram illustrating an
organic light emitting display device in accordance with the
present disclosure.
[0030] FIG. 2 is a cross-sectional view illustrating an organic
light emitting display device as an example of an organic light
emitting device in accordance with one exemplary aspect of the
present disclosure.
[0031] FIG. 3 is a cross-sectional view illustrating an organic
light emitting diode having single emitting part in accordance with
an exemplary aspect of the present disclosure.
[0032] FIG. 4 is a cross-sectional view illustrating an organic
light emitting diode having a double stack structure in accordance
with another exemplary aspect of the present disclosure.
[0033] FIG. 5 is a cross-sectional view illustrating an organic
light emitting display device in accordance with another exemplary
aspect of the present disclosure.
[0034] FIG. 6 is a cross-sectional view illustrating an organic
light emitting diode having a double stack structure in accordance
with still another exemplary aspect of the present disclosure.
[0035] FIG. 7 is a cross-sectional view illustrating an organic
light emitting diode having a triple stack structure in accordance
with still further another exemplary aspect of the present
disclosure.
[0036] FIG. 8 is a cross-section view illustrating an organic light
emitting display device in accordance with still another exemplary
aspect of the present disclosure.
DETAILED DESCRIPTION
[0037] Reference will now be made in detail to embodiments of the
disclosure, examples of which are illustrated in the accompanying
drawings.
[0038] The organic light emitting diode of the present disclosure
can enhance its luminous efficiency and its luminous lifespan by
applying particular organic compounds into an emitting material
layer, an electron blocking layer and/or a hole blocking layer. The
organic light emitting diode can be applied into an organic light
emitting device such as an organic light emitting display device or
an organic light emitting illumination device.
[0039] FIG. 1 is a schematic circuit diagram illustrating an
organic light emitting display device of the present disclosure. As
illustrated in FIG. 1, a gate line GL, a data line DL and power
line PL, each of which cross each other to define a pixel region P,
are formed in the organic light emitting display device. A
switching thin film transistor Ts, a driving thin film transistor
Td, a storage capacitor Cst and an organic light emitting diode D
are formed within the pixel region P. The pixel region P may
include a red (R) pixel region, a green (G) pixel region and a blue
(B) pixel region.
[0040] The switching thin film transistor Ts is connected to the
gate line GL and the data line DL, and the driving thin film
transistor Td and the storage capacitor Cst are connected between
the switching thin film transistor Ts and the power line PL. The
organic light emitting diode D is connected to the driving thin
film transistor Td. When the switching thin film transistor Ts is
turned on by a gate signal applied into the gate line GL, a data
signal applied into the data line DL is applied into a gate
electrode of the driving thin film transistor Td and one electrode
of the storage capacitor Cst through the switching thin film
transistor Ts.
[0041] The driving thin film transistor Td is turned on by the data
signal applied into the gate electrode so that a current
proportional to the data signal is supplied from the power line PL
to the organic light emitting diode D through the driving thin film
transistor Td. And then, the organic light emitting diode D emits
light having a luminance proportional to the current flowing
through the driving thin film transistor Td. In this case, the
storage capacitor Cst is charge with a voltage proportional to the
data signal so that the voltage of the gate electrode in the
driving thin film transistor Td is kept constant during one frame.
Therefore, the organic light emitting display device can display a
desired image.
[0042] FIG. 2 is a schematic cross-sectional view illustrating an
organic light emitting display device in accordance with an
exemplary aspect of the present disclosure. As illustrated in FIG.
2, the organic light emitting display device 100 comprises a
substrate 102, a thin-film transistor Tr over the substrate 102,
and an organic light emitting diode D connected to the thin film
transistor Tr. As an example, the substrate 102 defines a red pixel
region, a green pixel region and a blue pixel region and the
organic light emitting diode D is located in each pixel region. In
other words, the organic light emitting diode D, each of which
emits red, green or blue (B) light, is located correspondingly in
the red pixel region, the green pixel region and the blue pixel
region.
[0043] The substrate 102 may include, but is not limited to, glass,
thin flexible material and/or polymer plastics. For example, the
flexible material may be selected from, but is not limited to,
polyimide (PI), polyethersulfone (PES), polyethylenenaphthalate
(PEN), polyethylene terephthalate (PET), polycarbonate (PC) and
combination thereof. The substrate 102, over which the thin film
transistor Tr and the organic light emitting diode D are arranged,
forms an array substrate.
[0044] A buffer layer 106 may be disposed over the substrate 102,
and the thin film transistor Tr is disposed over the buffer layer
106. The buffer layer 106 may be omitted.
[0045] A semiconductor layer 110 is disposed over the buffer layer
106. In one exemplary aspect, the semiconductor layer 110 may
include, but is not limited to, oxide semiconductor materials. In
this case, a light-shield pattern may be disposed under the
semiconductor layer 110, and the light-shield pattern can prevent
light from being incident toward the semiconductor layer 110, and
thereby, preventing the semiconductor layer 110 from being
deteriorated by the light. Alternatively, the semiconductor layer
110 may include polycrystalline silicon. In this case, opposite
edges of the semiconductor layer 110 may be doped with
impurities.
[0046] A gate insulating layer 120 including an insulating material
is disposed on the semiconductor layer 110. The gate insulating
layer 120 may include, but is not limited to, an inorganic
insulating material such as silicon oxide (SiO.sub.x) or silicon
nitride (SiN.sub.x).
[0047] A gate electrode 130 made of a conductive material such as a
metal is disposed over the gate insulating layer 120 so as to
correspond to a center of the semiconductor layer 110. While the
gate insulating layer 120 is disposed over a whole area of the
substrate 102 in FIG. 2, the gate insulating layer 120 may be
patterned identically as the gate electrode 130.
[0048] An interlayer insulating layer 140 including an insulating
material is disposed on the gate electrode 130 with covering over
an entire surface of the substrate 102. The interlayer insulating
layer 140 may include an inorganic insulating material such as
silicon oxide (SiO.sub.x) or silicon nitride (SiN.sub.x), or an
organic insulating material such as benzocyclobutene or
photo-acryl.
[0049] The interlayer insulating layer 140 has first and second
semiconductor layer contact holes 142 and 144 that expose both
sides of the semiconductor layer 110. The first and second
semiconductor layer contact holes 142 and 144 are disposed over
opposite sides of the gate electrode 130 with spacing apart from
the gate electrode 130. The first and second semiconductor layer
contact holes 142 and 144 are formed within the gate insulating
layer 120 in FIG. 2. Alternatively, the first and second
semiconductor layer contact holes 142 and 144 are formed only
within the interlayer insulating layer 140 when the gate insulating
layer 120 is patterned identically as the gate electrode 130.
[0050] A source electrode 152 and a drain electrode 154, which are
made of conductive material such as a metal, are disposed on the
interlayer insulating layer 140. The source electrode 152 and the
drain electrode 154 are spaced apart from each other with respect
to the gate electrode 130, and contact both sides of the
semiconductor layer 110 through the first and second semiconductor
layer contact holes 142 and 144, respectively.
[0051] The semiconductor layer 110, the gate electrode 130, the
source electrode 152 and the drain electrode 154 constitute the
thin film transistor Tr, which acts as a driving element. The thin
film transistor Tr in FIG. 2 has a coplanar structure in which the
gate electrode 130, the source electrode 152 and the drain
electrode 154 are disposed over the semiconductor layer 110.
Alternatively, the thin film transistor Tr may have an inverted
staggered structure in which a gate electrode is disposed under a
semiconductor layer and a source and drain electrodes are disposed
over the semiconductor layer. In this case, the semiconductor layer
may include amorphous silicon.
[0052] Although not shown in FIG. 2, a gate line and a data line,
which cross each other to define a pixel region, and a switching
element, which is connected to the gate line and the data line, is
may be further formed in the pixel region. The switching element is
connected to the thin film transistor Tr, which is a driving
element. In addition, a power line is spaced apart in parallel from
the gate line or the data line, and the thin film transistor Tr may
further include a storage capacitor configured to constantly keep a
voltage of the gate electrode for one frame.
[0053] A passivation layer 160 is disposed on the source and drain
electrodes 152 and 154 with covering the thin film transistor Tr
over the whole substrate 102. The passivation layer 160 has a flat
top surface and a drain contact hole 162 that exposes the drain
electrode 154 of the thin film transistor Tr. While the drain
contact hole 162 is disposed on the second semiconductor layer
contact hole 144, it may be spaced apart from the second
semiconductor layer contact hole 144.
[0054] The organic light emitting diode (OLED) D includes a first
electrode 210 that is disposed on the passivation layer 160 and
connected to the drain electrode 154 of the thin film transistor
Tr. The organic light emitting diode D further includes an emissive
layer 230 and a second electrode 220 each of which is disposed
sequentially on the first electrode 210.
[0055] The first electrode 210 is disposed in each pixel region.
The first electrode 210 may be an anode and include conductive
material having relatively high work function value. For example,
the first electrode 210 may include, but is not limited to, a
transparent conductive oxide (TCO). Particularly, the first
electrode 210 may include indium tin oxide (ITO), indium zinc oxide
(IZO), indium tin zinc oxide (ITZO), SnO, ZnO, indium cerium oxide
(ICO), aluminum doped zinc oxide (AZO), and the like.
[0056] In one exemplary aspect, when the organic light emitting
display device 100 is a bottom-emission type, the first electrode
210 may have a single-layered structure of TCO. Alternatively, when
the organic light emitting display device 100 is a top-emission
type, a reflective electrode or a reflective layer may be disposed
under the first electrode 210. For example, the reflective
electrode or the reflective layer may include, but is not limited
to, silver (Ag) or aluminum-palladium-copper (APC) alloy. In the
organic light emitting display device 100 of the top-emission type,
the first electrode 210 may have a triple-layered structure of
ITO/Ag/ITO or ITO/APC/ITO.
[0057] In addition, a bank layer 164 is disposed on the passivation
layer 160 in order to cover edges of the first electrode 210. The
bank layer 164 exposes a center of the first electrode 210. The
bank layer 164 may be omitted.
[0058] An emissive layer 230 is disposed on the first electrode
210. In one exemplary embodiment, the emissive layer 230 may have a
mono-layered structure of an emitting material layer (EML).
Alternatively, the emissive layer 230 may have a multiple-layered
structure of a hole injection layer (HIL), a hole transport layer
(HTL), an electron blocking layer (EBL), an EML, a hole blocking
layer (HBL), an electron transport layer (ETL) and/or an electron
injection layer (EIL), as illustrated in FIGS. 3 and 4. The
emissive layer 230 may have a single emitting part or may have
multiple emitting parts to form a tandem structure.
[0059] The emissive layer 230 may include at least one emitting
material layer including an anthracene-based compound in which at
least one hydrogen atom is deuterated and a boron-based compound in
the blue pixel region, and at least one electron blocking layer
including an aryl amine-based compound. Alternatively, the emissive
layer 230 may further comprise at least one hole blocking layer
including at least one of an azine-based compound and a
benzimidazole-based compound. The emissive layer 230 enables the
OLED D and the organic light emitting display device 100 to improve
their luminous efficiency and luminous lifespan considerably.
[0060] The second electrode 220 is disposed over the substrate 102
above which the emissive layer 230 is disposed. The second
electrode 220 may be disposed over a whole display area, and may
include a conductive material with a relatively low work function
value compared to the first electrode 210, and may be a cathode.
For example, the second electrode 220 may include, but is not
limited to, high-reflective material such as aluminum (Al),
magnesium (Mg), calcium (Ca), silver (Ag), alloy thereof or
combination thereof such as aluminum-magnesium alloy (Al--Mg). When
the organic light emitting display device 100 is a top-emission
type, the second electrode 220 is thin so that it has light
transmissive (semi-transmissive) property.
[0061] In addition, an encapsulation film 170 may be disposed over
the second electrode 220 in order to prevent outer moisture from
penetrating into the organic light emitting diode D. The
encapsulation film 170 may have, but is not limited to, a laminated
structure of a first inorganic insulating film 172, an organic
insulating film 174 and a second inorganic insulating film 176. The
encapsulation film 170 may be omitted.
[0062] The organic light emitting display device 100 may further
include a polarizing plate to reduce reflection of external light.
For example, the polarizing plate may be a circular polarizing
plate. When the organic light emitting display device 100 is a
bottom-emission type, the polarizing plate may be located under the
substrate 102. Alternatively, when the organic light emitting
display device 100 is a top-emission type, the polarizing plate may
be attached onto the encapsulation film 170. Further, a cover
window may be attached onto the encapsulation film 170 or the
polarizing plate in the organic light emitting display device 100
of the top-emission type. In this case, the substrate 102 and the
cover window have flexible properties so that a flexible display
device can be constructed.
[0063] As described above, the emissive layer 230 in the organic
light emitting diode D includes particular compounds so that the
organic light emitting diode D can enhance its luminous efficiency
and its luminous lifespan. FIG. 3 is a schematic cross-sectional
view illustrating an organic light emitting diode having a single
emitting part in accordance with an exemplary embodiment of the
present disclosure.
[0064] As illustrated in FIG. 3, the organic light emitting diode
(OLED) D1 in accordance with the first embodiment of the present
disclosure includes first and second electrodes 210 and 220 facing
each other and an emissive layer 230 disposed between the first and
second electrodes 210 and 220. In an exemplary embodiment, the
emissive layer 230 includes an EML 340, which may be a first EML,
disposed between the first and second electrodes 210 and 220 and an
EBL 330, which may be a first EBL, disposed between the first
electrode 210 and the EML 340. Alternatively, the emissive layer
230 may further include a HBL 350, which may be a first HBL,
disposed between the EML 340 and the second electrode 220.
[0065] In addition, the emissive layer 230 may further include an
HIL 310 disposed between the first electrode 210 and the EBL 330
and an HTL 320 disposed between the HIL 310 and the EBL 330. In
addition, the emissive layer 230 may further include an EIL 360
disposed between the HBL 350 and the second electrode 220. In an
alternative embodiment, the emissive layer 230 may further include
an ETL disposed between the HBL 350 and the EIL 360. The organic
light emitting display device 100 (FIG. 2) includes a red pixel
region, a green pixel region and a blue pixel region, and the OLED
D1 may be located in the blue pixel region.
[0066] One of the first and second electrodes 210 and 220 may be an
anode and the other of the first and second electrodes 210 and 220
may be a cathode. Also, one of the first and second electrodes 210
and 220 may be a transmissive (semi-transmissive) electrode and the
other of the first and second electrodes 210 and 220 may be a
reflective electrode. For example, each of the first and second
electrodes 210 and 220 may have a thickness of, but is not limited
to, about 30 nm to about 300 nm.
[0067] The EML 340 includes a dopant 342, which may be a first
dopant, of a boron-based compound and a host 344, which may be a
first host, of an anthracene-based compound so that the EML 340
emits blue (B) light. In this case, the dopant 342 of the
boron-based compound may not be deuterated or may be partially
deuterated, while at least one hydrogen atoms in the host 344 of
the anthracene-based compound may be deuterated. Namely, the host
344 in the EML 340 may be partially or fully deuterated, while the
dopant 342 may not be deuterated or may be partially deuterated.
The dopant 342 of the boron-based compound may have the following
structure of Formula 1A or Formula 1B:
##STR00007## [0068] wherein each of R.sub.11 to R.sub.14 and each
of R.sub.21 to R.sub.24 is independently selected from the group
consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group, or adjacent two of R.sub.11 to R.sub.14 and R.sub.21 to
R.sub.24 form a fused ring, wherein each of the aryl group, the
aryl amino group, the hetero aryl group and the alicyclic group of
R.sub.11 to R.sub.14 and R.sub.21 to R.sub.24 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; each of R.sub.31 and R.sub.41 is independently
selected from the group consisting of hydrogen, a C.sub.1-C.sub.10
alkyl group, a C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl
amino group, a C.sub.5-C.sub.30 hetero aryl group and a
C.sub.3-C.sub.30 alicyclic group, wherein each of the aryl group,
the aryl amino group, the hetero aryl group and the alicyclic group
of R.sub.31 and R.sub.41 is independently unsubstituted or
substituted with at least one C.sub.1-C.sub.10 alkyl group;
R.sub.51 is selected form the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group, a C.sub.3-C.sub.15 cyclo alkyl group,
a C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group,
a C.sub.5-C.sub.30 hetero aryl group. a C.sub.3-C.sub.30 alicyclic
group and a C.sub.5-C.sub.30 hetero cyclic group, wherein each of
the cyclo alkyl group, the aryl group, the aryl amino group, the
hetero aryl group, the alicyclic group and the hetero cyclic group
of R.sub.51 is independently unsubstituted or substituted with at
least one C.sub.1-C.sub.10 alkyl group; when each of R.sub.31,
R.sub.41 and R.sub.51 is a C.sub.6-C.sub.30 aryl group substituted
with at least one C.sub.1-C.sub.10 alkyl group, the substituted
alkyl group is linked to each other to form a fused ring.
[0068] ##STR00008## [0069] wherein X is NR.sub.1, CR.sub.2R.sub.3,
O, S, Se or SiR.sub.4R.sub.5, each of R.sub.1 to R.sub.5 is
independently selected from the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group, a C.sub.6-C.sub.30 aryl group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group; each of R.sub.61 to R.sub.64 is independently selected from
the group consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.6-C.sub.30 aryl group, a C.sub.6-C.sub.30 aryl amino group, a
C.sub.5-C.sub.30 hetero aryl group and a C.sub.3-C.sub.30 alicyclic
group, or adjacent two of R.sub.61 to R.sub.64 form a fused ring,
wherein each of the aryl group, the aryl amino group, the hetero
aryl group and the alicyclic group of R.sub.61 to R.sub.64 is
independently unsubstituted or substituted with at least one
C.sub.1-C.sub.10 alkyl group; each of R.sub.71 to R.sub.74 is
independently selected from the group consisting of hydrogen, a
C.sub.1-C.sub.10 alkyl group and a C.sub.3-C.sub.30 alicyclic
group; R.sub.81 is selected from the group consisting of a
C.sub.6-C.sub.30 aryl group, a C.sub.5-C.sub.30 hetero aryl group
and a C.sub.3-C.sub.30 alicyclic group, or R.sub.81 and R.sub.61
form a fused ring, wherein each of the aryl group, the hetero aryl
group and the alicyclic group of R.sub.81 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; R.sub.82 is selected from the group consisting of a
C.sub.6-C.sub.30 aryl group, a C.sub.5-C.sub.30 hetero aryl group
and a C.sub.3-C.sub.30 alicyclic group, wherein each of the aryl
group, the hetero aryl group and the alicyclic group of R.sub.82 is
independently unsubstituted or substituted with at least one
C.sub.1-C.sub.10 alkyl group; R.sub.91 is selected from the group
consisting of hydrogen, a C.sub.1-C.sub.10 alkyl group, a
C.sub.3-C.sub.15 cyclo alkyl group, a C.sub.6-C.sub.30 aryl group,
a C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30 hetero aryl
group and a C.sub.3-C.sub.30 alicyclic group, wherein each of the
cyclo alkyl group, the aryl group, the aryl amino group, the hetero
aryl group and the alicyclic group of R.sub.91 is independently
unsubstituted or substituted with at least one C.sub.1-C.sub.10
alkyl group; when each of R.sub.81, R.sub.82 and R.sub.91 is a
C.sub.6-C.sub.30 aryl group substituted with at least one
C.sub.1-C.sub.10 alkyl group, the substituted alkyl group is linked
to each other to form a fused ring.
[0070] As an example, each of R.sub.11 to R.sub.14, R.sub.21 to
R.sub.24, R.sub.31 and R.sub.41 in Formula 1A may be independently
selected from the group consisting of hydrogen, a C.sub.1-C.sub.10
alkyl group, a C.sub.6-C.sub.30 aryl group and a C.sub.5-C.sub.30
hetero aryl group, wherein each of the aryl group and the hetero
aryl group of R.sub.11 to R.sub.14, R.sub.21 to R.sub.24, R.sub.31
and R.sub.41 may be independently unsubstituted or substituted with
a C.sub.1-C.sub.10 alkyl group, and R.sub.51 in Formula 1A may be
selected from the group consisting of C.sub.1-C.sub.10 alkyl group,
a C.sub.6-C.sub.30 aryl amino group, a C.sub.5-C.sub.30 hetero aryl
group and a C.sub.3-C.sub.30 hetero cyclic group, and wherein each
of the hetero aryl group, the aryl amino group and the hetero
cyclic group of R.sub.51 may be independently unsubstituted or
substituted with a C.sub.1-C.sub.10 alkyl group.
[0071] For example, one of R.sub.11 to R.sub.14 and/or one of
R.sub.21 to R.sub.24 may be a C.sub.1-C.sub.10 alkyl group and the
rest of R.sub.11 to R.sub.14 and/or the rest of R.sub.21 to
R.sub.24 may be hydrogen, and each of R.sub.31 and R.sub.41 may be
independently phenyl substituted with a C.sub.1-C.sub.10 alkyl
group or a dibenzofuranyl substituted with a C.sub.1-C.sub.10 alkyl
group in Formula 1A. R.sub.51 in Formula 1A may be a
C.sub.1-C.sub.10 alkyl group, a diphenyl amino group, a hetero aryl
group including nitrogen atom or a hetero cyclic group including a
nitrogen atom. In this case, the alkyl group may be, but is not
limited to, tert-butyl. In addition, the fused ring formed by
adjacent groups may be, but is not limited to, a C.sub.3-C.sub.10
alicyclic ring.
[0072] Alternatively, X in Formula 1B may be O or S, each of
R.sub.61 to R.sub.64 in Formula 1B may be independently selected
from the group consisting of hydrogen, a C.sub.1-C.sub.10 alkyl
group and a C.sub.6-C.sub.30 aryl amino group, or adjacent two of
R.sub.61 to R.sub.64 may form a fused ring, each of R.sub.71 to
R.sub.74 may be independently selected from the group consisting of
hydrogen and a C.sub.1-C.sub.10 alkyl group, R.sub.81 may be
selected from the group consisting of a C.sub.6-C.sub.30 aryl group
and a C.sub.5-C.sub.30 hetero aryl group, or R.sub.81 and R.sub.61
may form a fused ring, wherein each of the aryl group and the
hetero aryl group of R.sub.81 may be independently unsubstituted or
substituted with a C.sub.1-C.sub.10 alkyl group, R.sub.82 may be
selected from the group consisting of a C.sub.6-C.sub.30 aryl group
and a C.sub.5-C.sub.30 hetero aryl group, wherein each of the aryl
group and the hetero aryl group of R.sub.82 may be independently
unsubstituted or substituted with a C.sub.1-C.sub.10 alkyl group,
and wherein R.sub.91 may be a C.sub.1-C.sub.10 alkyl group.
[0073] For example, X in Formula 1B may be O. Each of R.sub.61 to
R.sub.64 may be independently selected from the group consisting of
protium, deuterium, a C.sub.1-C.sub.10 alkyl group and a diphenyl
amino group, or adjacent two of R.sub.61 to R.sub.64 may form a
fused ring, and the diphenyl amino group or the fused group may be
deuterated. Each of R.sub.71 to R.sub.74 may be independently
selected from the group consisting of protium, deuterium and a
C.sub.1-C.sub.10 alkyl group. Each of R.sub.81 and R.sub.82 may be
independently selected from the group consisting of phenyl and
dibenzofuranyl each of which may be independently unsubstituted or
substituted with deuterium and/or a C.sub.1-C.sub.10 alkyl group.
R.sub.91 may be a C.sub.1-C.sub.10 alkyl group such as tert-butyl,
but is not limited thereto.
[0074] Alternatively, R.sub.73 may be a C.sub.1-C.sub.10 alkyl
group and each of R.sub.71, R.sub.72 and R.sub.74 may be
independently protium or deuterium in Formula 1B. For example, in
the boron-based compound having the structure of Formula 1B, at
least one protium linked to the aromatic ring and the
heteroaromatic ring other than the aromatic ring linked to boron
atom and two nitrogen atoms and the aromatic rings fused by those
hetero aromatic rings may be substituted with deuterium. Namely,
R.sub.91 in Formula 1B may not be deuterated.
[0075] For example, the dopant 342 of the boron-based compound may
be selected from, but is not limited to, the following compounds of
Formula 2:
##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013##
##STR00014##
[0076] In another exemplary aspect, the host 344 of the
anthracene-based compound may have the following structure of
Formula 3:
##STR00015## [0077] wherein each of Ar1 and Ar2 is independently a
C.sub.6-C.sub.30 aryl group or a C.sub.5-C.sub.30 hetero aryl
group; L is a single bond, a C.sub.6-C.sub.20 arylene group or a
C.sub.5-C.sub.20 hetero arylene group; a is an integer of 0 to 8;
each of b, c and d is independently an integer of 0 to 30, wherein
at least one of a, b, c and d is a positive integer.
[0078] As an example, each of Ar1 and Ar2 may be independently
phenyl, naphthyl, dibenzofuranyl or a fused dibenzofuranyl and L
may be a single bond, phenylene or dibenzofuranylene in Formula 3.
For example, Ar1 may be naphthyl, dibenzofuranyl or fused
dibenzofuranyl and Ar2 may be phenyl or naphthyl in Formula 3.
Alternatively, both Ar1 and Ar2 may be naphthyl and L may be a
single bond, phenylene or dibenzofuranylene.
[0079] Particularly, 1-naphtyl moiety is linked directly to the
anthracene moiety, 2-naphthyl moiety is linked directly or via
phenylene linker (bridging group) to the anthracene moiety, and at
least one protium, for example, all protiums, in the molecule may
be deuterated.
[0080] For example, the host 344 of the anthracene-based compound
may be selected from, but is not limited to, the following compound
of Formula 4.
##STR00016## ##STR00017##
[0081] In one exemplary embodiment, the contents of the host 344
may be about 70 wt % to about 99.9 wt % and the contents of the
dopant 342 may be about 0.1 wt % to about 30 wt % in the EML 340.
For example, the contents of the dopant 342 in the EML 340 may be
about 0.1 wt % to about 10 wt %, for example, about 1 wt % to about
5 wt % so that the EML 340 may implement sufficient luminous
efficiency and luminous lifespan. The EML 340 may have a thickness
of, but is not limited to, about 10 nm to about 200 nm, for
example, about 20 nm to about 100 nm or about 20 nm to about 50
nm.
[0082] The EML 340 includes the dopant 342 of the boron-based
compound and the host 344 of the anthracene-based compound
substituted with at least one deuterium so that the OLED D1 and the
organic light emitting display device 100 can improve their
luminous efficiency and luminous lifespan. When the dopant 342 of
the boron-based compound has an asymmetric chemical structure such
as Formula 1B, the OLED D1 and the organic light emitting display
device 100 can improve their luminous efficiency and luminous
lifespan significantly.
[0083] In addition, when the EML 340 includes the dopant 342 where
a part of or all protiums linked to the aromatic rings and the
heteroaromatic rings other than the aromatic ring linked to boron
atom and two nitrogen atoms may be substituted with deuterium, the
OLED D1 and the organic light emitting display device 100 can
improve further their luminous efficiency and luminous
lifespan.
[0084] Moreover, when the EML 340 includes the host 344 of the
anthracene-based compound where two naphthyl moieties are linked to
directly or via a linker to the anthracene moiety and at least one,
for example all protiums are deuterated, the luminous efficiency
and the luminous lifespan of the OLED D1 and the organic light
emitting display device 100 can be further enhanced.
[0085] The HIL 310 is disposed between the first electrode 210 and
the HTL 320 and improves an interface property between the
inorganic first electrode 210 and the organic HTL 320. In one
exemplary embodiment, the HIL 310 may include a hole injection
material selected from, but is not limited to, the group consisting
of 4,4'4''-Tris(3-methylphenylamino)triphenylamine (MTDATA),
4,4',4''-Tris(N,N-diphenyl-amino)triphenylamine (NATA),
4,4',4''-Tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine
(1T-NATA),
4,4',4''-Tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine
(2T-NATA), Copper phthalocyanine (CuPc),
Tris(4-carbazoyl-9-yl-phenyl)amine (TCTA),
N,N'-Diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4''-diamine
(NPB; NPD), 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile
(Dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile;
HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB),
poly(3,4-ethylenedioxythiphene)polystyrene sulfonate (PEDOT/PSS),
2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ),
N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-
-fluoren-2-amine and combination thereof.
[0086] Alternatively, the HIL 340 may comprise a hole injection
host and a hole injection dopant. As an example, the hole injection
host may comprise a spirofluorene-based compound having the
following structure of Formula 11 and the hole injection dopant may
comprise a radialene-based compound having the following structure
of Formula 12, but is not limited thereto.
##STR00018##
[0087] When the HIL 310 includes the hole injection host and the
hole injection dopant, the contents of the hole injection dopant in
the HIL 310 may be, but is not limited to, about 1 wt % to about 50
wt %, for example, about 1 wt % to about 30 wt %. The HIL 310 may
be omitted in compliance of the OLED D1 property.
[0088] The HTL 320 is disposed between the HIL 310 and the EBL 330.
In one exemplary embodiment, the HTL 320 may include a hole
transport material selected from, but is not limited to,
N,N'-Diphenyl-N,N'-bis(3-methylphenyl-1,1'-biphenyl-4,4'-diamine
(TPD), NPB (NPD),
N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-biphenyl-
]-4,4'-diamine (DNTPD), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP),
Poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine]
(Poly-TPD),
Poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(4-sec-butylphenyl)diphe-
nylamine))] (TFB),
1,1-bis(4-(N,N'-di(p-tolyl)amino)phenyl)cyclohexane (TAPC),
3,5-Di(9H-carbazol-9-yl)-N,N-diphenylaniline (DCDPA),
N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-
-fluoren-2-amine,
N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)biphenyl-4-amine-
,
N-([1,1'-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenl-9H-carbazol-3-yl)phe-
nyl)-9H-fluoren-2-amine,
N4,N4,N4',N4'-tetrakis([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine
and/or the spirofluorene-based compound having the structure of
Formula 11.
[0089] In an exemplary embodiment, each of the HIL 310 and the HTL
320 may independently have a thickness of, but is not limited to,
about 5 nm to about 200 nm, for example, about 5 nm to about 100
nm.
[0090] The EBL 330 prevents electrons from transporting from the
EML 340 to the first electrode 210. The EBL 330 may include an
electron blocking material 332 of a spiroaryl amine-based compound
having the following structure of Formula 5:
##STR00019## [0091] wherein L.sub.3 is C.sub.6-C.sub.30 arylene; o
is 0 or 1; each of R.sub.121 and R.sub.122 is independently
C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30 hetero aryl, wherein each
of the C.sub.6-C.sub.30 aryl and the C.sub.5-C.sub.30 hetero aryl
is optionally substituted with at least one of C.sub.1-C.sub.10
alkyl and C.sub.6-C.sub.30 aryl, respectively.
[0092] As an example, L.sub.3 may be phenylene and each of
R.sub.121 to R.sub.122 may be independently unsubstituted or
substituted with at least one of C.sub.1-C.sub.10 alkyl and
C.sub.6-C.sub.30 aryl (e.g. phenyl), and may be selected from the
group consisting of phenyl, biphenyl, fluorenyl, carbazolyl, phenyl
carbazolyl, carbazolyl phenyl, dibenzofuranyl and
dibenzothiophenyl.
[0093] For example, the electron blocking material 332 may be
selected from any spiroaryl amine-based compounds having the
following structure of Formula 6:
##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024##
##STR00025## ##STR00026## ##STR00027## ##STR00028##
##STR00029##
[0094] Alternatively, the OLED D1 may further include the HBL 350
which prevents holes from transporting from the EML 340 to the
second electrode 220. As an example, the HBL 350 may include a hole
blocking material 352 of an azine-based compound having the
following structure of Formula 7 and/or a benzimidazole-based
compound having the following structure of Formula 9.
##STR00030## [0095] wherein each of Y.sub.1 to Y.sub.5 is
independently CR.sub.131 or N, one to three of Y.sub.1 to Y.sub.5
is N, and R.sub.131 is a C.sub.6-C.sub.30 aryl group; L is a
C.sub.6-C.sub.30 arylene group; R.sub.132 is a C.sub.6-C.sub.30
aryl group or a C.sub.5-C.sub.30 hetero aryl group, wherein the
C.sub.6-C.sub.30 aryl group is optionally substituted with another
C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30 hetero aryl or forms a
spiro structure with a C.sub.10-C.sub.30 fused aryl ring or a
C.sub.10-C.sub.30 fused hetero aryl ring, wherein the another
C.sub.6-C.sub.30 aryl is optionally further substituted with other
C.sub.6-C.sub.30 aryl or C.sub.5-C.sub.30 hetero aryl or forms a
spiro structure with a C.sub.10-C.sub.30 fused aryl ring; R.sub.133
is hydrogen or adjacent two of R.sub.133 form a fused aromatic
ring; r is 0 or 1; s is 1 or 2; and t is an integer of 0 to 4;
[0095] ##STR00031## [0096] wherein Ar is C.sub.10-C.sub.30 arylene;
R.sub.141 is a C.sub.6-C.sub.30 aryl group or a C.sub.5-C.sub.30
hetero aryl group, each of the C.sub.6-C.sub.30 aryl group and the
C.sub.5-C.sub.30 hetero aryl group is optionally substituted with
C.sub.1-C.sub.10 alkyl; and each of R.sub.142 and R.sub.143 is
independently hydrogen, a C.sub.1-C.sub.10 alkyl group or a
C.sub.6-C.sub.30 aryl group.
[0097] In one exemplary embodiment, the aryl group constituting
R.sub.132 in Formula 7 may be unsubstituted or substituted further
with another C.sub.6-C.sub.30 aryl group or C.sub.5-C.sub.30 hetero
aryl group, or form a spiro structure with other fused aryl ring or
fused hetero aryl ring. For example, the aryl or the hetero aryl
group that may be substituted to R.sub.132 may be a
C.sub.10-C.sub.30 fused aryl group or a C.sub.10-C.sub.30 fused
hetero aryl group. R.sub.133 in Formula 7 may be fused to form a
naphthyl group. In one exemplary embodiment, the azine-based
compound as the hole blocking material 352 may be selected from any
azine-based compounds having the following structure of Formula
8:
##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036##
##STR00037## ##STR00038## ##STR00039##
[0098] As an example, "Ar" in Formula 9 may be a naphthylene group
or an anthracenylene group, R.sub.141 in Formula 9 may be a phenyl
group or a benzimidazole group, R.sub.142 in Formula 9 may be a
methyl group, an ethyl group or a phenyl group and R.sub.143 in
Formula 9 may be hydrogen, a methyl group or a phenyl group. In one
exemplary embodiment, the benzimidazole compound as the hole
blocking material 352 may be selected from any benzimidazole-based
compounds having the following structure of Formula 10.
##STR00040##
[0099] In an exemplary embodiment, each of the EBL 330 and the HBL
350 may independently have a thickness of, but is not limited to,
about 5 nm to about 200 nm, for example, about 5 nm to about 100
nm.
[0100] The compound having the structure of Formulae 7 to 10 has
good electron transport property as well as excellent hole blocking
property. Accordingly, the HBL 350 including the compound having
the structure of Formulae 7 to 10 may function as a hole blocking
layer and an electron transport layer.
[0101] In an alternative embodiment, the OLED D1 may further
include an ETL disposed between the HBL 350 and the EIL 360. In one
exemplary embodiment, the ETL may include, but is not limited to,
oxadiazole-based compounds, triazole-based compounds,
phenanthroline-based compounds, benzoxazole-based compounds,
benzothiazole-based compounds, benzimidazole-based compounds,
triazine-based compounds, and the like.
[0102] Particularly, the ETL may include an electron transport
material selected from, but is not limited to, the group consisting
of tris-(8-hydroxyquinoline) aluminum (Alq.sub.3),
2-biphenyl-4-yl-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD),
spiro-PBD, lithium quinolate (Liq),
1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzene (TPBi),
Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)alumin-
um (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen),
2,9-Bis(naphthalene-2-yl)4,7-diphenyl-1,10-phenanthroline (NBphen),
2,9-Dimethyl-4,7-diphenyl-1,10-phenathroline (BCP),
3-(4-Biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ),
4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),
1,3,5-Tri(p-pyrid-3-yl-phenyl)benzene (TpPyPB),
2,4,6-Tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine
(TmPPPyTz),
Poly[9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alt-
-2,7-(9,9-dioctylfluorene)] (PFNBr), tris(phenylquinoxaline) (TPQ),
Diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1),
2-[4-(9,10-Di-2-naphthalenyl-2-anthracenyl)phenyl]-1-phenyl-1H-benzimdazo-
le (ZADN), 1,3-bis(9-phenyl-1,10-phenathrolin-2-yl)benzene,
1,4-bis(2-phenyl-1,10-phenanthrolin-4-yl)benzene (p-bPPhenB) and/or
1,3-bis(2-phenyl-1,10-phenanthrolin-4-yl)benzene (m-bPPhenB).
[0103] The EIL 360 is disposed between the HBL 350 and the second
electrode 220, and can improve physical properties of the second
electrode 320 and therefore, can enhance the life span of the OLED
D1. In one exemplary embodiment, the EIL 360 may include, but is
not limited to, an alkali metal halide or alkaline earth metal
halide such as LiF, CsF, NaF, BaF.sub.2 and the like, and/or an
organic metal compound such as Liq, lithium benzoate, sodium
stearate, and the like.
[0104] In an alternative embodiment, the EIL 360 may be an organic
layer doped with the alkali metal such as Li, Na, K and/or Cs
and/or the alkaline earth metal such as Mg, Sr, Ba and/or Ra. An
organic host used in the EIL 360 may be the electron transport
material and the contents of the alkali metal and/or the alkaline
earth metal in the EIL 360 may be, but is not limited to, about 1
wt % to about 30 wt %. For example, the EIL 360 may include an
electron transport material having the following structure of
Formula 13:
##STR00041##
[0105] As an example, each of the ETL and the EIL 360 may
independently have a thickness of, but is not limited to, about 10
nm to about 200 nm, for example, about 10 nm to 100 nm.
[0106] The OLED D1 can maximize its luminous efficiency and
luminous lifespan by applying the dopant 342 of the boron-based
compound having the structure of Formulae 1A to 2 and the host 344
of the anthracene-based compound having the structure of Formulae 3
to 4 into the EML 340, the aryl amine-based compound having the
structure of Formulae 5 and 6 into the EBL 330, and optionally the
azine-based compound having the structure of Formulae 7 to 8 and/or
the benzimidazole-based compound having the structure of Formulae 9
to 10 into the HBL 350.
[0107] In the first exemplary embodiment, the OLED D1 may have
single emitting part. An OLED in accordance with the present
disclosure may have a tandem structure including multiple emitting
parts. FIG. 4 is a schematic cross-sectional view illustrating an
organic light emitting diode having two emitting parts in
accordance with another exemplary embodiment of the present
disclosure.
[0108] As illustrated in FIG. 4, the OLED D2 in accordance with the
second embodiment of the present disclosure includes first and
second electrodes 210 and 220 facing each other and an emissive
layer 230A disposed between the first and second electrodes 210 and
220. The emissive layer 230A includes a first emitting part 400
disposed between the first electrode 210 and the second electrode
220, a second emitting part 500 disposed between the first emitting
part 400 and the second electrode 220 and a charge generation layer
(CGL) 470 disposed between the first and second emitting parts 400
and 500. The organic light emitting display device 100 (FIG. 2)
includes the red pixel region, the green pixel region and the blue
pixel region, and the OLED D2 may be located in the blue pixel
region.
[0109] One of the first and second electrodes 210 and 220 may be an
anode and the other of the first and second electrodes 210 and 220
may be a cathode. Also, one of the first and second electrodes 210
and 220 may be a transmissive (semi-transmissive) electrode and the
other of the first and second electrodes 210 and 220 may be a
reflective electrode.
[0110] The first emitting part 400 includes a first emitting
material layer (EML1) 440 disposed between the first electrode 210
and the CGL 470. The first emitting part 400 may include a first
electron blocking layer (EBL1) 430 disposed between the first
electrode 210 and the EML1 440, and optionally a first hole
blocking layer (HBL1) 450 disposed between the EML1 440 and CGL
470. In addition, the first emitting part 400 may further include
an HIL 410 disposed between the first electrode 210 and the EBL1
430 and a first hole transport layer (HTL1) 420 disposed between
the HIL 410 and the EBL1 430.
[0111] The second emitting part 500 includes a second emitting
material layer (EML2) 540 disposed between the CGL 470 and the
second electrode 220. The second emitting part 500 may include a
second electron blocking layer (EBL2) 530 disposed between the CGL
470 and the EML2 540, and optionally a second hole blocking layer
(HBL2) 550 disposed between the EML2 540 and the second electrode
220. In addition, the second emitting part 500 may further include
a second hole transport layer (HTL2) 520 disposed between the CGL
470 and EBL2 530 and an EIL 560 disposed between the HBL2 550 and
the second electrode 220. Each of the HIL 410, the HTL1 420, the
HTL2 520 and the EIL 560 may independently include the same
material as described above. The HTL1 420 may include the same
material as or different material from the HTL2 520.
[0112] The EML1 440 includes a first dopant 442 of a boron-based
compound and a first host 444 of an anthracene-based compound so
that the EML1 440 emits blue (B) light. The EML2 540 includes a
second dopant 542 of a boron-based compound and a second host 544
of an anthracene-based compound so that the EML2 540 emits blue (B)
light.
[0113] Each of the first dopant 442 and the second dopant 542 of
the born-based compound may not be deuterated or partially
deuterated, and may have independently the structure of Formulae 1A
to 2. Each of the first host 444 and the second host 544 of the
anthracene-based compound may be at least partially deuterated, and
may have independently the structure of Formulae 3 to 4. The first
dopant 442 may be identical to or different from the second dopant
542, and the first host 444 may be identical to or different from
the second host 544.
[0114] In one exemplary embodiment, each of the contents of the
first host 444 and the second host 544 may be independently about
70 wt % to about 99.9 wt % and each of the contents of the first
dopant 442 and the second dopant 542 may be independently about 0.1
wt % to about 30 wt % in the EML1 440 and in the EML2 540,
respectively. For example, the contents of the first dopant 442 and
the second dopant 542 in the EML1 440 and in the EML2 540,
respectively, may be about 0.1 wt % to about 10 wt %, for example,
about 1 wt % to about 5 wt % so that both the EML1 440 and the EML2
540 can implement sufficient luminous efficiency and luminous
lifespan.
[0115] Each of the EBL1 430 and the EBL2 530 prevents electrons
from transporting from the EML1 440 or EML2 540 to the first
electrode 210 or the CGL 470, respectively. Each of the EBL1 430
and the EBL2 530 may include a first electron blocking material 432
and a second electron blocking material 532, respectively. Each of
the first electron blocking material 432 and the second electron
blocking material 532 may comprise independently the amine-based
compound having the structure of Formulae 5 to 6, respectively. The
first electron blocking material 432 may be identical to or
different from the second electron blocking material 532.
[0116] Each of the HBL1 450 and the HBL2 550 prevents holes from
transporting from the EML1 440 or EML2 540 to the CGL 470 or the
second electrode 220, respectively. Each of the HBL1 450 and the
HBL2 550 may include a first hole blocking material 452 and a
second hole blocking material 552, respectively. Each of the first
hole blocking material 452 and the second hole blocking material
552 may comprise independently the azine-based compound having the
structure of Formulae 7 to 8 and/or the benzimidazole-based
compound having the structure of Formulae 9 to 10, respectively.
The first hole blocking material 452 may be identical to or
different from the second hole blocking material 552.
[0117] As described above, the compound having the structure of
Formulae 7 to 10 has excellent electron transport property as well
as excellent hole blocking property. Therefore, each of the HBL1
450 and the HBL2 550 may function as a hole blocking layer and an
electron transport layer.
[0118] In an alternative embodiment, the first emitting part 400
may further include a first electron transport layer (ETL1)
disposed between the HBL1 450 and the CGL 470 and/or the second
emitting part 500 may further include a second electron transport
layer (ETL2) disposed between the HBL2 550 and the EIL 560.
[0119] The CGL 470 is disposed between the first emitting part 400
and the second emitting part 500 so that the first emitting part
400 and the second emitting part 500 are connected via the CGL 470.
The CGL 470 may be a PN-junction CGL having an N-type CGL (N-CGL)
480 and a P-type CGL (P-CGL) 490. The N-CGL 480 is disposed between
the HBL1 450 and the HTL2 520 and the P-CGL 490 is disposed between
the N-CGL 480 and the HTL2 520. The N-CGL 480 injects electrons
into the first emitting part 400 and the P-CGL 490 injects holes
into the second emitting part 500.
[0120] As an example, the N-CGL 480 may be an organic layer doped
with an alkali metal such as Li, Na, K and/or Cs and/or an alkaline
earth metal such as Mg, Sr, Ba and/or Ra. For example, an organic
host used in the N-CGL 480 may include, but is not limited to, an
organic compound such as Bphen or MTDATA. The alkali metal and/or
the alkaline earth metal may be doped by about 0.01 wt % to about
30 wt % in the N-type CGL 480.
[0121] The P-CGL 490 may include, but is not limited to, an
inorganic material selected from the group consisting of tungsten
oxide (WO.sub.x), molybdenum oxide (MoO.sub.x), beryllium oxide
(Be.sub.2O.sub.3), vanadium oxide (V.sub.2O.sub.5) and combination
thereof, and/or an organic material selected from the group
consisting of NPD, HAT-CN, F4TCNQ, TPD,
N,N,N',N'-Tetranaphthalenyl-benzidine (TNB), TCTA,
N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8) and
combination thereof.
[0122] Alternatively, the P-CGL 490 may include a P-type host
having the structure of Formula 11 and a P-type dopant having the
structure of Formula 12. When the P-CGL 490 includes the P-type
host and the P-type dopant, the contents of the P-type dopant in
the P-CGL 490 may be, but is not limited to, about 1 wt % to about
50 wt %, for example, about 1 wt % to about 30 wt %.
[0123] Each of the EML1 440 and the EML2 540 includes the first and
second dopants 442 and 542 of the boron-based compound and the
first and second hosts 444 and 544 of the anthracene-based compound
where at least one carbon atoms are deuterated, respectively. Each
of the first and second dopants 442 and 542 of the boron-based
compound may have independently an asymmetric chemical structure
such as Formula 1B and may not be deuterated or partially
deuterated. Also, each of the first and second hosts 444 and 544 of
the anthracene-based compound may have a structure where two
naphthyl moieties are linked directly or via the linker to the
anthracene moiety and at least one protium, for example, all
protiums are deuterated. Accordingly, the OLED D2 and the organic
light emitting display device 100 can improve their luminous
efficiency and luminous lifespan.
[0124] In addition, the OLED D2 and the organic light emitting
display device 100 can maximize their luminous efficiency and
luminous lifespan by applying the aryl amine-based compound having
the structure of Formulae 5 and 6 into the EBL1 430 and the EBL2
530 as the first and second electron blocking materials 432 and
532, respectively, and optionally the azine-based compound having
the structure of Formulae 7 to 8 and/or the benzimidazole-based
compound having the structure of Formulae 9 to 10 into the HBL1 450
and the HBL2 550 as the first and second hole blocking materials
452 and 552, respectively. In addition, the organic light emitting
display device 100 (See, FIG. 2) can implement an image having high
color purity by laminating double stack structure of two emitting
parts 400 and 500 each of which emits blue color light.
[0125] In the second embodiment, the OLED D2 has a tandem structure
of two emitting parts. Alternatively, an OLED may include three or
more emitting parts, for example, may include a second CGL and a
third emitting part disposed on the second emitting parts 500
except the EIL 560 (See, FIG. 7).
[0126] In the above embodiment, the organic light emitting display
device 100 and the OLEDs D1 and D2 implement blue (B) emission.
Alternatively, an organic light emitting display device and an OLED
can implement a full color display device including white (W)
emission. FIG. 5 is a schematic cross-sectional view illustrating
an organic light emitting display device in accordance with another
exemplary embodiment of the present disclosure.
[0127] As illustrated in FIG. 5, the organic light emitting display
device 600 comprises a first substrate 602 that defines each of a
red pixel region RP, a green pixel region GP and a blue pixel
region BP, a second substrate 604 facing the first substrate 602, a
thin film transistor Tr over the first substrate 602, an organic
light emitting diode D disposed between the first and second
substrates 602 and 604 and emitting white (W) light and a color
filter layer 680 disposed between the organic light emitting diode
D and the second substrate 604.
[0128] Each of the first and second substrates 602 and 604 may
include, but is not limited to, glass, flexible material and/or
polymer plastics. For example, each of the first and second
substrates 602 and 604 may be made of PI, PES, PEN, PET, PC and
combination thereof. The first substrate 602, over which a thin
film transistor Tr and an organic light emitting diode D are
arranged, forms an array substrate.
[0129] A buffer layer 606 may be disposed over the first substrate
602, and the thin film transistor Tr is disposed over the buffer
layer 606 correspondingly to each of the red pixel region RP, the
green pixel region GP and the blue pixel region BP. The buffer
layer 606 may be omitted.
[0130] A semiconductor layer 610 is disposed over the buffer layer
606. The semiconductor layer 610 may be made of oxide semiconductor
material or polycrystalline silicon.
[0131] A gate insulating layer 620 including an insulating
material, for example, inorganic insulating material such as
silicon oxide (SiO.sub.x) or silicon nitride (SiN.sub.x) is
disposed on the semiconductor layer 610.
[0132] A gate electrode 630 made of a conductive material such as a
metal is disposed over the gate insulating layer 620 so as to
correspond to a center of the semiconductor layer 610. An
interlayer insulting layer 640 including an insulating material,
for example, inorganic insulating material such as silicon oxide
(SiO.sub.x) or silicon nitride (SiN.sub.x), or an organic
insulating material such as benzocyclobutene or photo-acryl, is
disposed on the gate electrode 630.
[0133] The interlayer insulating layer 640 has first and second
semiconductor layer contact holes 642 and 644 that expose both
sides of the semiconductor layer 610. The first and second
semiconductor layer contact holes 642 and 644 are disposed over
opposite sides of the gate electrode 630 with spacing apart from
the gate electrode 630.
[0134] A source electrode 652 and a drain electrode 654, which are
made of a conductive material such as a metal, are disposed on the
interlayer insulating layer 640. The source electrode 652 and the
drain electrode 654 are spaced apart from each other with respect
to the gate electrode 630, and contact both sides of the
semiconductor layer 610 through the first and second semiconductor
layer contact holes 642 and 644, respectively.
[0135] The semiconductor layer 610, the gate electrode 630, the
source electrode 652 and the drain electrode 654 constitute the
thin film transistor Tr, which acts as a driving element.
[0136] Although not shown in FIG. 5, a gate line and a data line,
which cross each other to define a pixel region, and a switching
element, which is connected to the gate line and the data line, may
be further formed in the pixel region. The switching element is
connected to the thin film transistor Tr, which is a driving
element. In addition, a power line is spaced apart in parallel from
the gate line or the data line, and the thin film transistor Tr may
further include a storage capacitor configured to constantly keep a
voltage of the gate electrode for one frame.
[0137] A passivation layer 660 is disposed on the source and drain
electrodes 652 and 654 with covering the thin film transistor Tr
over the whole first substrate 602. The passivation layer 660 has a
drain contact hole 662 that exposes the drain electrode 654 of the
thin film transistor Tr.
[0138] The organic light emitting diode (OLED) D is located over
the passivation layer 660. The OLED D includes a first electrode
710 that is connected to the drain electrode 654 of the thin film
transistor Tr, a second electrode 720 facing from the first
electrode 710 and an emissive layer 730 disposed between the first
and second electrodes 710 and 720.
[0139] The first electrode 710 formed for each pixel region may be
an anode and may include a conductive material having relatively
high work function value, for example, TCO. As an example, the
first electrode 710 may include, ITO, IZO, ITZO, SnO, ZnO, ICO,
AZO, and the like.
[0140] When the organic light emitting display device 600 is a
bottom-emission type, the first electrode 710 may have a
single-layered structure of TCO. Alternatively, when the organic
light emitting display device 600 is a top-emission type, a
reflective electrode or a reflective layer may be disposed under
the first electrode 710. For example, the reflective electrode or
the reflective layer may include, but is not limited to, Ag or APC
alloy. In the organic light emitting display device 600 of the
top-emission type, the first electrode 710 may have a
triple-layered structure of ITO/Ag/ITO or ITO/APC/ITO.
[0141] A bank layer 664 is disposed on the passivation layer 660 in
order to cover edges of the first electrode 710. The bank layer 664
exposes a center of the first electrode 710 corresponding to each
of the red pixel region RP, the green pixel region GP and the blue
pixel region BP. The bank layer 664 may be omitted.
[0142] An emissive layer 730 including multiple emitting parts is
disposed on the first electrode 710. Since the OLED D emits white
light in each of the red, green and blue pixel regions RP, GP and
BP, the emissive layer 730 may be formed of a common layer without
separating in the red, green and blue pixel regions RP, GP and
BP.
[0143] As illustrated in FIGS. 6 and 7, the emissive layer 730 may
include multiple emitting parts 800, 900, 1000, 1100 and 1200 and
at least one charge generation layer 870, 1070 and 1170. Each of
the emitting parts 800, 900, 1000, 1100 and 1200 may include EML
and may further include at least one of HIL, HTL, EBL, HBL, ETL
and/or EIL.
[0144] The second electrode 720 is disposed over the first
substrate 602 above which the emissive layer 730 is disposed. The
second electrode 720 may be disposed over a whole display area, and
may include a conductive material with a relatively low work
function value compared to the first electrode 710, and may be a
cathode. For example, the second electrode 720 may include, but is
not limited to, Al, Mg, Ca, Ag, alloy thereof and combination
thereof such as Al--Mg.
[0145] Since the light emitted from the emissive layer 730 is
incident to the color filter layer 680 through the second electrode
720 in the organic light emitting display device 600 in accordance
with the second embodiment of the present disclosure, the second
electrode 720 has a thin thickness so that the light can be
transmitted.
[0146] The color filter layer 680 is disposed over the OLED D and
includes a red color filter 682, a green color filter 684 and a
blue color filter 686 each of which is disposed correspondingly to
the red pixel region RP, the green pixel region GP and the blue
pixel region BP, respectively. Although not shown in FIG. 5, the
color filter layer 680 may be attached to the OLED through an
adhesive layer. Alternatively, the color filter layer 680 may be
disposed directly on the OLED D.
[0147] In addition, an encapsulation film may be disposed over the
second electrode 720 in order to prevent outer moisture from
penetrating into the OLED D. The encapsulation film may have, but
is not limited to, a laminated structure of a first inorganic
insulating film, an organic insulating film and a second inorganic
insulating film (See, 170 in FIG. 2). In addition, the organic
light emitting display device 600 may further include a polarizing
plate.to reduce reflection of external light. For example, the
polarizing plate may be a circular polarizing plate. When the
organic light emitting display device 600 is a bottom-emission
type, the polarizing plate may be located under the first substrate
602. Alternatively, when the organic light emitting display device
600 is a top emission type, the polarizing plate may be located
over the second substrate 604.
[0148] In FIG. 5, the light emitted from the OLED D is transmitted
through the second electrode 720 and the color filter layer 680 is
disposed over the OLED D. Alternatively, the light emitted from the
OLED D is transmitted through the first electrode 710 and the color
filter layer 680 may be disposed between the OLED D and the first
substrate 602. In addition, a color conversion layer may be formed
between the OLED D and the color filter layer 680. The color
conversion layer may include a red color conversion layer, a green
color conversion layer and a blue color conversion layer each of
which is disposed correspondingly to each pixel region (RP, GP and
BP), respectively, so as to covert the white (W) color light to
each of a red, green and blue color lights, respectively.
[0149] As described above, the white (W) color light emitted from
the OLED D is transmitted through the red color filter 682, the
green color filter 684 and the blue color filter 686 each of which
is disposed correspondingly to the red pixel region RP, the green
pixel region GP and the blue pixel region BP, respectively, so that
red, green and blue color lights are displayed in the red pixel
region RP, the green pixel region GP and the blue pixel region
BP.
[0150] FIG. 6 is a schematic cross-sectional view illustrating an
organic light emitting diode having a tandem structure of two
emitting parts. As illustrated in FIG. 6, the organic light
emitting diode (OLED) D3 in accordance with the exemplary
embodiment includes first and second electrodes 710 and 720 and an
emissive layer 730 disposed between the first and second electrodes
710 and 720. The emissive layer 730 includes a first emitting part
800 disposed between the first and second electrodes 710 and 720, a
second emitting part 900 disposed between the first emitting part
800 and the second electrode 720 and a charge generation layer
(CGL) 870 disposed between the first and second emitting parts 800
and 900.
[0151] One of the first and second electrodes 710 and 720 may be an
anode and the other of the first and second electrodes 710 and 720
may be a cathode. Also, one of the first and second electrodes 710
and 720 may be a transmissive (semi-transmissive) electrode and the
other of the first and second electrodes 710 and 720 may be a
reflective electrode.
[0152] In addition, one of the first and second emitting parts 800
and 900 emit blue (B) light and the other of the first and second
emitting parts 800 and 900 emits red-green (RG) or yellow-green
(YG) light. Hereinafter, the OLED D3 where the first emitting part
800 emits blue (B) light and the second emitting part 900 emits
red-green (RG) and/or yellow-green (YG) light will be described in
detail.
[0153] The first emitting part 800 includes an EML1 840 disposed
between the first electrode 710 and the CGL 870. The first emitting
part 800 may include an EBL1 830 disposed between the first
electrode 710 and the EML1 840, and optionally an HBL1 850 disposed
between the EML1 840 and the CGL 870. In addition, the first
emitting part 800 may further include an HIL 810 disposed between
the first electrode and the EBL1 830 and an HTL1 820 disposed
between the HIL 810 and the EBL1 830. Alternatively, the first
emitting part 800 may further include an ETL1 disposed between the
HBL1 850 and the CGL 870.
[0154] The second emitting part 900 includes an EML2 940 disposed
between the CGL 870 and the second electrode 720. The second
emitting part 900 may include an HTL 920 disposed between the CGL
870 and the EML2 940 and an ETL2 950 disposed between the second
electrode 720 and the EML2 940 and an EIL 960 disposed between the
second electrode 720 and the ETL2 950. Alternatively, the second
emitting part 900 may further include an EBL2 disposed between the
HTL2 920 and the EML2 940 and/or an HBL2 disposed between the EML2
940 and the ETL2 950.
[0155] The CGL 870 is disposed between the first emitting part 800
and the second emitting part 900. The CGL 870 may be a PN-junction
CGL having an N-CGL 870 and a P-CGL 890. The N-CGL 880 is disposed
between the HBL1 850 and the HTL2 920 and the P-CGL 890 is disposed
between the N-CGL 880 and the HTL2 920.
[0156] Each of the HIL 810, the HTL1 820, the HTL2 920, the EIL 560
and the CGL 870 may independently include the same material as
described above. The HTL1 820 may include the same material as or
different material from the HTL2 920.
[0157] The EML1 840 includes a first dopant 842 of a boron-based
compound and a first host 844 of an anthracene-based compound so
that the EML1 840 emits blue (B) light. The first dopant 842 of the
born-based compound may not be deuterated or partially deuterated,
and may have the structure of Formulae 1A to 2. The first host 844
of the anthracene-based compound may be at least partially
deuterated, and may have the structure of Formulae 3 to 4.
[0158] In one exemplary embodiment, the contents of the first host
844 may be about 70 wt % to about 99.9 wt % and the contents of the
first dopant 842 may be about 0.1 wt % to about 30 wt % in the EML1
840. For example, the contents of the first dopant 844 in the EML1
840 may be about 0.1 wt % to about 10 wt %, for example, about 1 wt
% to about 5 wt % so that the EML1 840 can implement sufficient
luminous efficiency and luminous lifespan.
[0159] The EBL1 830 prevents electrons from transporting from the
EML1 840 to the first electrode 710 and may include an electron
blocking material 832. The electron blocking material 832 may
include the amine-based compound having the structure of Formulae 5
to 6.
[0160] The HBL1 850 prevent holes from transporting form the EML1
840 to the CGL 870 and may include a hole blocking material 852.
The hole blocking material 852 may include the azine-based compound
having the structure of Formulae 7 to 8 and/or the
benzimidazole-based compound having the structure of Formulae 9 to
10. As described above, the compound having the structure of
Formulae 7 to 10 has excellent electron transport property as well
as excellent hole blocking property. Therefore, the HBL1 850 may
function as a hole blocking layer and an electron transport
layer.
[0161] In one exemplary aspect, the EML2 940 may emit yellow-green
(YG) light. For example, the EML2 940 may include yellow-green (YG)
dopant 943 and a host 945.
[0162] The host 945 in the EML2 940 may include, but is not limited
to, 9,9'-Diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), CBP,
1,3,5-Tris(carbazole-9-yl)benzene (TCP), TCTA,
4,4'-Bis(carbazole-9-yl)-2,2'-dimethylbipheyl (CDBP),
2,7-Bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP),
2,2',7,7'-Tetrakis(carbazole-9-yl)-9,9-spirofluorene (Spiro-CBP),
Bis[2-(diphenylphosphine)phenyl] ether oxide (DPEPO),
4'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (PCzB-2CN),
3'-(9H-carbazol-9-yl)biphenyl-3,5-dicarbonitrile (mCzB-2CN),
3,6-Bis(carbazole-9-yl)-9-(2-ethyl-hexyl)-9H-carbazole (TCz1),
Bis(2-hydroxylphenyl)-pyridine)beryllium (Bepp2),
Bis(10-hydroxylbenzo[h] quinolinato)beryllium (Bebg2) and/or
1,3,5-Tris(1-pyrenyl)benzene (TPB3).
[0163] The yellow-green (YG) dopant 943 may include at least one of
yellow-green (YG) fluorescent material, yellow-green (YG)
phosphorescent material and yellow-green (YG) delayed fluorescent
material. As an example, the yellow-green (YG) dopant 943 may
include, but is not limited to, 5,6,11,12-Tetraphenylnaphthalene
(Rubrene),
2,8-Di-tert-butyl-5,11-bis(4-tert-butylphenyl)-6,12-diphenyltetracene
(TBRb), Bis(2-phenylbenzothiazolato)(acetylacetonate)iridium(III)
(Ir(BT).sub.2(acac)),
Bis(2-(9,9-diethytl-fluoren-2-yl)-1-phenyl-1H-benzo[d]imdiazolato)(acetyl-
acetonate)iridium(III) (Ir(fbi).sub.2(acac)),
Bis(2-phenylpyridine)(3-(pyridine-2-yl)-2H-chromen-2-onate)iridium(III)
(fac-Ir(ppy).sub.2Pc),
Bis(2-(2,4-difluorophenyl)quinoline)(picolinate)iridium(III)
(FPQIrpic), and the like.
[0164] Alternatively, the EML2 940 may emit red-green (RG) light.
In this case, the EML2 940 may include green (G) and red (R) dopant
943 and a host 945. In this case, the EML2 940 may have a
single-layered structure including the host, green (G) dopant and
red (R) dopant, or may have a double-layered structure comprising a
lower layer (first layer) including a host and green (G) dopant (or
red (R) dopant) and an upper layer (second layer) including a host
and red (R) dopant (or green (G) dopant).
[0165] The host 945 in the EML2 940 emitting red-green (RG) light
may be the same as the host emitting yellow-green (YG) light.
[0166] The green (G) dopant 943 in the EML2 940 may include at
least one of green fluorescent material, green phosphorescent
material and green delayed fluorescent material. As an example, the
green (G) dopant 943 may include, but is not limited to,
[Bis(2-phenylpyridine)](pyridyl-2-benzofuro[2,3-b]pyridine)iridium,
fac-Tris(2-phenylpyridine)iridium(III) (fac-Ir(ppy).sub.3),
Bis(2-phenylpyridine)(acetylacetonate)iridium(III)
(Ir(ppy).sub.2(acac)), Tris[2-(p-tolyl)pyridine]iridium(III)
(Ir(mppy).sub.3),
Bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium(III)
(Ir(npy).sub.2acac), Tris(2-phenyl-3-methyl-pyridine)iridium
(Ir(3mppy).sub.3), fac-Tris(2-(3-p-xylyl)phenyl)pyridine
iridium(III) (TEG), and the like
[0167] The red (R) dopant 943 in the EML2 940 may include at least
one of red fluorescent material, red phosphorescent material and
red delayed fluorescent material. As an example, the red (R) dopant
943 may include, but is not limited to,
[Bis(2-(4,6-dimethyl)phenylquinoline)](2,2,6,6-tetramethylheptane-3,5-dio-
nate)iridium(III),
Bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III)
(Hex-Ir(phq).sub.2(acac)),
Tris[2-(4-n-hexylphenyl)quinoline]iridium(III) (Hex-Ir(phq).sub.3),
Tris[2-phenyl-4-methylquinoline]iridium(III) (Ir(Mphq).sub.3),
Bis(2-phenylquinoline)(2,2,6,6-tetramethylheptene-3,5-dionate)iridium(III-
) (Ir(dpm)PQ.sub.2),
Bis(phenylisoquinoline)(2,2,6,6-tetramethylheptene-3,5-dionate)iridium(II-
I) (Ir(dpm)(piq).sub.2),
Bis[(4-n-hexylphenyl)isoquinoline](acetylacetonate)iridium(III)
(Hex-Ir(piq).sub.2(acac)),
Tris[2-(4-n-hexylphenyl)quinoline]iridium(III) (Hex-Ir(piq).sub.3),
Tris(2-(3-methylphenyl)-7-methyl-quinolato)iridium
(Ir(dmpq).sub.3),
Bis[2-(2-methylphenyl)-7-methyl-quinoline](acetylacetonate)iridium(III)
(Ir(dmpq).sub.2(acac)),
Bis[2-(3,5-dimethylphenyl)-4-methyl-quinoline](acetylacetonate)iridium(II-
I) (Ir(mphmq).sub.2(acac)), and the like.
[0168] In an alternative aspect, the EML2 940 may have a
triple-layered structure of a first layer including a host and red
(R) dopant, a second layer including a host and yellow-green (YG)
dopant and a third layer including a host and green (G) dopant.
[0169] When the EML2 940 emits red-green (RG) or yellow-green (YG)
light, the contents of the host 945 may be about 70 wt % to about
99.9 wt % and the contents of the dopant 943 may be about 0.01 wt %
to about 30 wt %, respectively, in the EML2 940. For example, the
contents of the dopant 943 in the EML2 940 may be about 0.1 wt % to
about 10 wt %, for example, about 1 wt % to about 5 wt % so that
the EML2 940 can implement sufficient luminous efficiency and
luminous lifespan.
[0170] Each of the ETL1 and the ETL2 950 may include independently
oxadiazole-based compounds, triazole-based compounds,
phenanthroline-based compounds, benzoxazole-based compounds,
benzothiazole-based compounds, benzimidazole-based compounds,
triazine-based compounds, and the like. For example, each of the
ETL1 and the ETL2 950 may include independently electron transport
material selected from, but is not limited to, Alq.sub.3, PBD,
spiro-PBD, Liq, TPBi, BAlq, Bphen, NBphen, BCP, TAZ, NTAZ, TpPyPB,
TmPPPyTz, PFNBr, TPQ, TSPO1, ZADN,
1,3-bis(9-phenyl-1,10-phenathrolin-2-yl)benzene, p-bPPhenB,
m-bPPhenB and combination thereof.
[0171] The EBL2, which may be disposed between the HTL2 920 and the
EML2 940, may include a second electron blocking material. As an
example, the second electron blocking material may include the
amine-based compound having the structure of Formulae 5 to 6.
[0172] Alternatively, the EBL2 may include, but is not limited to,
TCTA, Tris[4-(diethylamino)phenyl]amine,
N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-
-fluorene-2-amine, TAPC, MTDATA, 1,3-bis(carbazol-9-yl)benzene
(mCP), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), CuPc, DNTPD, TDAPB,
DCDPA, 2,8-bis(9-phneyl-9H-carbazol-3-yl)dibenzo[b,d]thiophene,
3,6-bis(N-carbazolyl)-N-phenyl-carbazole and combination
thereof.
[0173] The HBL2, which may be disposed between the EML2 940 and the
ETL2 960, may include a second hole blocking material. As an
example, the second hole blocking material may include the
azine-based compound having the structure of Formulae 7 to 8 and/or
the benzimidazole-based compound having the structure of Formulae 9
to 10. Alternatively, the HBL2 may include oxadiazole-based
compounds, triazole-based compounds, phenanthroline-based
compounds, benzoxazole-based compounds, benzothiazole-based
compounds, benzimidazole-based compounds, triazine-based compounds,
and the like, which can be used as the electron transport material
in the ETL2 950.
[0174] In the OLED D3, the EML1 840 includes the dopant 842 of the
boron-based compound and the host 844 of the anthracene-based
compound in which at least one protium is substituted with
deuterium, and the EML2 940 emits red-green (RG) and/or
yellow-green (YG) light. Alternatively, the EML1 840 may emit
red-green (RG) and/or yellow green light and the EML2 940 may
include the dopant 842 of the boron-based compound and the host 844
of the anthracene-based compound to emit blue (B) light.
[0175] In the OLED D3, the EML1 840 includes the dopant 842 of the
boron-based compound and the host 844 of the anthracene-based
compound which is at least partially deuterated. The dopant 842 of
the boron-based compound may have an asymmetric chemical structure
such as Formula 1B and may not be deuterated or partially
deuterated. Also, the host 844 of the anthracene-based compound may
have a structure where two naphthyl moieties are linked directly or
via the linker to the anthracene moiety and at least one protium,
for example, all protiums are deuterated. Accordingly, the OLED D3
and the organic light emitting display device 600 can improve their
luminous efficiency and luminous lifespan.
[0176] In addition, the OLED D3 and the organic light emitting
display device 600 can maximize their luminous efficiency and
luminous lifespan by applying the aryl amine-based compound having
the structure of Formulae 5 and 6 into the EBL1 830 as the first
electron blocking materials 832, and optionally the azine-based
compound having the structure of Formulae 7 to 8 and/or the
benzimidazole-based compound having the structure of Formulae 9 to
10 into the HBL1 850 as the first hole blocking layers 852.
[0177] Alternatively, an organic light emitting diode may have
three or more emitting parts. FIG. 7 is a schematic cross-sectional
view illustrating an organic light emitting diode in accordance
with still another exemplary aspect of the present disclosure. As
illustrated in FIG. 7, the organic light emitting diode (OLED) D4
includes first and second electrodes 710 and 720 facing each other
and an emissive layer 730A disposed between the first and second
electrodes 710 and 720. The emissive layer 730A includes a first
emitting part 1000 disposed between the first and second electrodes
710 and 720, a second emitting part 1100 disposed between the first
emitting part 1000 and the second electrode 720, a third emitting
part 1200 disposed between the second emitting part 1100 and the
second electrode 720, a first charge generation layer (CGL1) 1070
disposed between the first and second emitting parts 1000 and 1100,
and a second charge generation layer (CGL2) 1170 disposed between
the second and third emitting parts 1100 and 1200.
[0178] At least one of the first to third emitting parts 1000, 1100
and 1200 may emit blue (B) light and at least another of the first
to third emitting parts 1000, 1100 and 1200 may emit red green (RG)
or yellow green (YG) light. Hereinafter, the OLED D4, where the
first and third emitting parts 1000 and 1200 emit blue (B) light
and the second emitting part 1100 emits red green (RG) and/or
yellow green (YG) light, will be explained in detail.
[0179] The first emitting part 1000 includes an EML1 1040 disposed
between the first electrode 710 and the CGL1 1070. The first
emitting part 1000 may include an EBL1 1030 disposed between the
first electrode 710 and the EML1 1040, and optionally an HBL1 1050
disposed between the EML1 1040 and the CGL1 1070. In addition, the
first emitting part 1000 may further include an HIL 1010 disposed
between the first electrode 710 and the EBL1 1030, an HTL1 1020
disposed between the HIL 1010 and the EBL1 1030, and optionally a
first electron transport layer (ETL1) disposed between the HBL1
1050 and the CGL1 1070.
[0180] The second emitting part 1100 includes an EML2 1140 disposed
between the CGL1 1070 and the CGL2 1170. The second emitting part
1100 may include an HTL2 1120 disposed between the CGL1 1070 and
the EML2 1140 and an ETL2 1150 disposed between the EML2 1140 and
the CGL2 1170. In addition, the second emitting part 1100 may
further include an EBL2 disposed between the HTL2 1120 and the EML2
1140 and/or an HBL2 disposed between the EML2 1140 and the ETL2
1150.
[0181] The third emitting part 1200 includes a third emitting
material layer (EML3) 1240 disposed between the CGL2 1170 and the
second electrode 720. The third emitting part 1200 may include a
third electron blocking layer (EBL3) 1230 disposed between the CGL2
1170 and the EML3 1240, and optionally a third hole blocking layer
(HBL3) 1250 disposed between the EML3 1240 and the second electrode
720. In addition, the third emitting part 1200 may further include
a third hole transport layer (HTL3) 1220 disposed between the CGL2
1170 and the EBL3 1230, an EIL 1260 disposed between the HBL3 1250
and the second electrode 720, and optionally a third electron
transport layer (ETL3) disposed between the HBL3 1250 and the EIL
1260.
[0182] The CGL1 1070 is disposed between the first emitting part
1000 and the second emitting part 1100. The CGL1 1070 may be a
PN-junction CGL having a first N-type CGL (N-CGL1) 1080 and a first
P-type CGL (P-CGL1) 1090. The N-CGL1 1080 is disposed between the
HBL1 1050 and the HTL2 1120 and the P-CGL1 1090 is disposed between
the N-CGL1 1080 and the HTL2 1120. The N-CGL1 1080 injects
electrons into the first emitting part 1000 and the P-CGL1 1090
injects holes into the second emitting part 1100.
[0183] The CGL2 1170 is disposed between the second emitting part
1100 and the third emitting part 1200. The CGL2 1170 may be a
PN-junction CGL having a second N-type CGL (N-CGL2) 1180 and a
second P-type CGL (P-CGL2) 1190. The N-CGL2 1080 is disposed
between the ETL2 1150 and the HTL3 1220 and the P-CGL2 1190 is
disposed between the N-CGL2 1180 and the HTL3 1220. The N-CGL2 1180
injects electrons into the second emitting part 1100 and the P-CGL2
1190 injects holes into the third emitting part 1200.
[0184] Each of the HIL 1010, the HTL1 1020, the HTL2 1120, the HTL3
1130, the EIL 120, the CGL1 1070 and the CGL2 1170 may
independently include the same material as described above. Each of
the HTL1 1020, the HTL2 1120 and the HTL3 1220 may comprise the
same material or different material to each other. In addition, the
CGL1 1070 may comprise the same material as or different material
from the CGL2 1170.
[0185] The EML1 1040 includes a first dopant 1042 of a boron-based
compound and a first host 1044 of an anthracene-based compound so
that the EML1 1040 emits blue (B) light. The EML3 1240 includes a
second dopant 1242 of a boron-based compound and a second host 1244
of an anthracene-based compound so that the EML3 1240 emits blue
(B) light.
[0186] Each of the first dopant 1042 and the second dopant 1242 of
the born-based compound may not be deuterated or partially
deuterated, and may have independently the structure of Formulae 1A
to 2. Each of the first host 1044 and the second host 1244 of the
anthracene-based compound may be at least partially deuterated, and
may have independently the structure of Formulae 3 to 4. The first
dopant 1042 may be identical to or different from the second dopant
1242, and the first host 1044 may be identical to or different from
the second host 1244.
[0187] In one exemplary embodiment, each of the contents of the
first host 1044 and the second host 1244 may be independently about
70 wt % to about 99.9 wt % and each of the contents of the first
dopant 1042 and the second dopant 1242 may be independently about
0.1 wt % to about 30 wt % in the EML1 1040 and in the EML3 1240,
respectively. For example, the contents of the first dopant 1042
and the second dopant 1242 in the EML1 1040 and in the EML3 1240,
respectively, may be about 0.1 wt % to about 10 wt %, for example,
about 1 wt % to about 5 wt % so that both the EML1 1040 and the
EML3 1240 can implement sufficient luminous efficiency and luminous
lifespan.
[0188] Each of the EBL1 1030 and the EBL3 1230 prevents electrons
from transporting from the EML1 1040 or EML3 1240 to the first
electrode 710 or the CGL2 1170, respectively. Each of the EBL1 1030
and the EBL3 1230 may include a first electron blocking material
1032 and a third electron blocking material 1232, respectively.
Each of the first electron blocking material 1032 and the third
electron blocking material 1232 may comprise independently the
amine-based compound having the structure of Formulae 5 to 6,
respectively. The first electron blocking material 1032 may be
identical to or different from the third electron blocking material
1232.
[0189] Each of the HBL1 1050 and the HBL3 1250 prevents holes from
transporting from the EML1 1040 or EML3 1240 to the CGL1 1070 or
the second electrode 720, respectively. Each of the HBL1 1050 and
the HBL3 1250 may include a first hole blocking material 1052 and a
third hole blocking material 1252, respectively. Each of the first
hole blocking material 1052 and the third hole blocking material
1252 may comprise independently the azine-based compound having the
structure of Formulae 7 to 8 and/or the benzimidazole-based
compound having the structure of Formulae 9 to 10, respectively.
The first hole blocking material 1052 may be identical to or
different from the third hole blocking material 1252.
[0190] As described above, the compound having the structure of
Formulae 7 to 10 has excellent electron transport property as well
as excellent hole blocking property. Therefore, each of the HBL1
1050 and the HBL3 1250 may function as a hole blocking layer and an
electron transport layer.
[0191] In one exemplary aspect, the EML2 1140 may emit yellow-green
(YG) light. For example, the EML2 1140 may include yellow-green
(YG) dopant 1143 and a host 1145.
[0192] Alternatively, the EML2 1140 may emit red-green (RG) light
and may include red (R) dopant and green (G) dopant 1143 and a host
1145. In this case, the EML2 1140 may have a single-layered
structure including the host, green (G) dopant and red (R) dopant,
or may have a double-layered structure comprising a lower layer
(first layer) including a host and green (G) dopant (or red (R)
dopant) and an upper layer (second layer) including a host and red
(R) dopant (or green (G) dopant).
[0193] In an alternative aspect, the EML2 1140 may have a
triple-layered structure of a first layer including a host and red
(R) dopant, a second layer including a host and yellow-green (YG)
dopant and a third layer including a host and green (G) dopant. The
dopant 1143 and the host 1145 in the EML2 1140 may be identical to
the corresponding materials as described above referring to FIG.
6.
[0194] Each of the ETL1, the ETL2 1150, the ETL3, the EBL2 disposed
between the HTL2 1120 and the EML2 1140 and the HBL2 disposed
between the EML2 1140 and the ETL2 1150 may comprise the identical
compounds to the corresponding material as described above.
[0195] Each of the EML1 1040 and the EML3 1240 includes the first
and second dopants 1042 and 1242 of the boron-based compound and
the first and second hosts 1044 and 1244 of the anthracene-based
compound where at least one carbon atoms are deuterated,
respectively. Each of the first and second dopants 1042 and 1242 of
the boron-based compound may have independently an asymmetric
chemical structure such as Formula 1B and may not be deuterated or
partially deuterated. Also, each of the first and second hosts 1044
and 1244 of the anthracene-based compound may have a structure
where two naphthyl moieties are linked directly or via the linker
to the anthracene moiety and at least one protium, for example, all
protiums are deuterated. Accordingly, the OLED D4 and the organic
light emitting display device 600 can improve their luminous
efficiency and luminous lifespan.
[0196] In addition, the OLED D4 and the organic light emitting
display device 600 can maximize their luminous efficiency and
luminous lifespan by applying the aryl amine-based compound having
the structure of Formulae 5 and 6 into the EBL1 1030 and the EBL3
1230 as the first and third electron blocking materials 1032 and
1232, respectively, and optionally the azine-based compound having
the structure of Formulae 7 to 8 and/or the benzimidazole-based
compound having the structure of Formulae 9 to 10 into the HBL1
1050 and the HBL3 1250 as the first and third hole blocking
materials 1052 and 1252, respectively. In addition, the OLED D4
includes the first and third emitting parts 1000 and 1020 each of
which emits blue (B) light and the second emitting part 1100
emitting yellow-green (YG) or red-green (RG) light so that the OLED
D4 can emit white (W) light
[0197] In FIG. 7, a tandem-structured OLED D4 having three emitting
parts are illustrated. Alternatively, an OLED may further include
at least one additional emitting parts and at least one additional
charge generation layer.
[0198] In addition, an organic light emitting device in accordance
with the present disclosure may include a color conversion layer.
FIG. 8 is a schematic cross-sectional view illustrating an organic
light emitting display device in still another exemplary embodiment
of the present disclosure.
[0199] As illustrated in FIG. 8, the organic light emitting display
device 1300 comprises a first substrate 1302 that defines each of a
red pixel region RP, a green pixel region GP and a blue pixel
region BP, a second substrate 1304 facing the first substrate 1302,
a thin film transistor Tr over the first substrate 1302, an organic
light emitting diode (OLED) D disposed between the first and second
substrates 1302 and 1304 and emitting blue (B) light and a color
conversion layer 1380 disposed between the OLED D and the second
substrate 1304. Although not shown in FIG. 8, a color filter layer
may be disposed between the second substrate 1304 and the
respective color conversion layer 1380.
[0200] The thin film transistor Tr is disposed over the first
substrate 1302 correspondingly to each of the red pixel region RP,
the green pixel region GP and the blue pixel region BP. A
passivation layer 1360, which has a drain contact hole 1362
exposing one electrode, for example a drain electrode, constituting
the thin film transistor Tr, is formed with covering the thin film
transistor Tr over the whole first substrate 1302.
[0201] The OLED D, which includes a first electrode 1410, an
emissive layer 1430 and the second electrode 1420, is disposed over
the passivation layer 1360. The first electrode 1410 may be
connected to the drain electrode of the thin film transistor Tr
through the drain contact hole 1362. In addition, a bank layer 1364
covering edges of the first electrode 1410 is formed at the
boundary between the red pixel region RP, the green pixel region GP
and the blue pixel region BP. In this case, the OLED D may have a
structure of FIG. 3 or FIG. 4 and can emit blue (B) light. The OLED
D is disposed in each of the red pixel region RP, the green pixel
region GP and the blue pixel region BP to provide blue (B)
light.
[0202] The color conversion layer 1380 may include a first color
conversion layer 1382 corresponding to the red pixel region RP and
a second color conversion layer 1384 corresponding to the green
pixel region GP. As an example, the color conversion layer 1380 may
include an inorganic luminescent material such as quantum dot
(QD).
[0203] The blue (B) light emitted from the OLED D in the red pixel
region RP is converted into red (R) color light by the first color
conversion layer 1382 and the blue (B) light emitted from the OLED
D in the green pixel region GP is converted into green (G) color
light by the second color conversion layer 1384. Accordingly, the
organic light emitting display device 1300 can implement a color
image.
[0204] In addition, when the light emitted from the OLED D is
displayed through the first substrate 1302, the color conversion
layer 1380 may be disposed between the OLED D and the first
substrate 1302.
Synthesis Example 1: Synthesis of Compound 1-1
[0205] (1) Synthesis of Intermediate 1-1C
##STR00042##
[0206] Compound 1-1A (69.2 g, 98 mmol), Compound 1-1B (27.6 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-1C (58.1 g, yield: 84%).
[0207] (2) Synthesis of Compound 1-1
##STR00043##
[0208] The Intermediate 1-1C (11.9 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at room
temperature (RT) for 1 hour. N,N-diisopropyl ethyl amine (3.2 g, 25
mmol) was added dropwisely to the solution at 0.degree. C., and
then the solution was stirred at 120.degree. C. for 2 hours. After
the reaction was complete, sodium acetate aqueous solution was
added into the reaction vessel at RT, and then the solution was
stirred. An organic layer was extracted with ethyl acetate and was
concentrated, and then a crude product was purified with column
chromatography to give Compound 1-1 (2.3 g, yield: 20%).
Synthesis Example 2: Synthesis of Compound 1-4
[0209] (1) Synthesis of Intermediate 1-4C
##STR00044##
[0210] Compound 1-4A (43.1 g, 98 mmol), Compound 1-4B (27.6 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-4C (57.1 g, yield:
85%).
[0211] (2) Synthesis of Compound 1-4
##STR00045##
[0212] The Intermediate 1-4C (8.6 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-4 (1.9 g, yield: 23%).
Synthesis Example 3: Synthesis of Compound 1-6
[0213] (1) Synthesis of Intermediate 1-6C
##STR00046##
[0214] Compound 1-6A (58.9 g, 98 mmol), Compound 1-6B (33.2 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-6C (59.7 g, yield:
75%).
[0215] (2) Synthesis of Compound 1-6
##STR00047##
[0216] The Intermediate 1-6C (10.1 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-6 (1.9 g, yield: 21%).
Synthesis Example 4: Synthesis of Compound 1-8
[0217] (1) Synthesis of Intermediate 1-8C
##STR00048##
[0218] Compound 1-8A (33.0 g, 98 mmol), Compound 1-8B (45.7 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-8C (54.1 g, yield:
72%).
[0219] (2) Synthesis of Compound 1-8
##STR00049##
[0220] The Intermediate 1-8C (9.6 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-8 (2.0 g, yield: 21%).
Synthesis Example 5: Synthesis of Compound 1-11
[0221] (1) Synthesis of Intermediate 1-11C
##STR00050##
[0222] Compound 1-11A (28.4 g, 98 mmol), Compound 1-11B (52.0 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-11C (39.9 g, yield:
52%).
[0223] (2) Synthesis of Compound 1-11
##STR00051##
[0224] The Intermediate 1-11C (9.8 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-11 (1.4 g, yield: 15%).
Synthesis Example 6: Synthesis of Compound 1-12
[0225] (1) Synthesis of Intermediate 1-12C
##STR00052##
[0226] Compound 1-12A (28.0 g, 98 mmol), Compound 1-12B (51.6 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-12C (44.1 g, yield:
58%).
[0227] (2) Synthesis of Compound 1-12
##STR00053##
[0228] The Intermediate 1-12C (9.7 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-12 (1.7 g, yield: 18%).
Synthesis Example 7: Synthesis of Compound 1-13
[0229] (1) Synthesis of Intermediate 1-13C
##STR00054##
[0230] Compound 1-13A (34.8 g, 98 mmol), Compound 1-13B (46.6 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-13C (41.3 g, yield:
53%).
[0231] (2) Synthesis of Compound 1-13
##STR00055##
[0232] The Intermediate 1-13C (9.9 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-13 (1.4 g, yield: 15%).
Synthesis Example 8: Synthesis of Compound 1-17
[0233] (1) Synthesis of Intermediate 1-17C
##STR00056##
[0234] Compound 1-17A (33.4 g, 98 mmol), Compound 1-17B (46.1 g, 98
mmol), palladium acetate (0.45 g, 2 mmol), sodium tert-butoxide
(18.9 g, 196 mmol), tri-tert-butylphosphine (0.8 g, 4 mmol) and
toluene (300 ml) were put into a 500 ml reaction vessel, and then
the solution was refluxed for 5 hours with stirring. After the
reaction was complete, the solution was filtered, and then the
filtrate was concentrated. A crude product was purified with column
chromatography to give the Intermediate 1-17C (47.1 g, yield:
62%).
[0235] (2) Synthesis of Compound 1-17
##STR00057##
[0236] The Intermediate 1-17C (9.7 g, 12.5 mmol) and tert-butyl
benzene (60 ml) were put into a 500 ml reaction vessel. N-butyl
lithium (45 ml, 37.5 mmol) was added dropwisely into the reaction
vessel at -78.degree. C., and then the solution was stirred at
60.degree. C. for 3 hours. Nitrogen gas was blown into the reaction
vessel at 60.degree. C. to remove a byproduct, boron tribromide
(6.3 g, 25 mmol) was added dropwisely to the solution at
-78.degree. C., and then the solution was stirred at RT for 1 hour.
N,N-diisopropyl ethyl amine (3.2 g, 25 mmol) was added dropwisely
to the solution at 0.degree. C., and then the solution was stirred
at 120.degree. C. for 2 hours. After the reaction was complete,
sodium acetate aqueous solution was added into the reaction vessel
at RT, and then the solution was stirred. An organic layer was
extracted with ethyl acetate and was concentrated, and then a crude
product was purified with column chromatography to give Compound
1-17 (1.6 g, yield: 17%).
Synthesis Example 9: Synthesis of Compound 2-1
##STR00058##
[0238] Compound 2-1A (2.0 g, 5.2 mmol), Compound 2-1B (1.5 g, 5.7
mmol), tris(dibenzylideneacetone)dipalladium(0)
(Pd.sub.2(dba).sub.3, 0.24 g, 0.26 mmol) and toluene (50 ml) were
put into a 250 ml reaction vessel in a dry box. The reaction vessel
was removed from the dry box, and then sodium carbonate anhydrous
(2M, 20 ml) was added into the solution. The reactants were stirred
and heated at 90.degree. C. overnight. The reaction was monitored
by HPLC (high-performance liquid chromatography). After the
solution was cooled to RT, an organic layer was separated. An
aqueous layer was washed with dichloromethane and the organic layer
was concentrated with rotary evaporation to obtain a gray powder.
The gray powder was purified with alumina, precipitated with
hexane, and purified with silica-gel column chromatography to give
Compound 2-1 (2.3 g, yield: 86%) of white powder.
Synthesis Example 10: Synthesis of Compound 2-2
##STR00059##
[0240] Compound 2-2A (2.0 g, 5.2 mmol), Compound 2-2B (1.5 g, 5.7
mmol), Pd.sub.2(dba).sub.3 (0.24 g, 0.26 mmol) and toluene (50 ml)
were put into a 250 ml reaction vessel in a dry box. The reaction
vessel was removed from the dry box, and then sodium carbonate
anhydrous (2M, 20 ml) was added into the solution. The reactants
were stirred and heated at 90.degree. C. overnight. The reaction
was monitored by HPLC. After the solution was cooled to RT, an
organic layer was separated. An aqueous layer was washed with
dichloromethane and the organic layer was concentrated with rotary
evaporation to obtain a gray powder. The gray powder was purified
with alumina, precipitated with hexane, and purified with
silica-gel column chromatography to give Compound 2-2 (2.0 g,
yield: 89%) of white powder.
Synthesis Example 11: Synthesis of Compound 2-3
##STR00060##
[0242] Compound 2-3A (2.0 g, 6.0 mmol), Compound 2-3B (1.9 g, 6.6
mmol), Pd.sub.2(dba).sub.3 (0.3 g, 0.3 mmol) and toluene (50 ml)
were put into a 250 ml reaction vessel in a dry box. The reaction
vessel was removed from the dry box, and then sodium carbonate
anhydrous (2M, 20 ml) was added into the solution. The reactants
were stirred and heated at 90.degree. C. overnight. The reaction
was monitored by HPLC. After the solution was cooled to RT, an
organic layer was separated. An aqueous layer was washed with
dichloromethane and the organic layer was concentrated with rotary
evaporation to obtain a gray powder. The gray powder was purified
with alumina, precipitated with hexane, and purified with
silica-gel column chromatography to give Compound 2-3 (2.0 g,
yield: 79%) of white powder.
Synthesis Example 12: Synthesis of Compound 2-4
##STR00061##
[0244] Compound 2-4A (2.0 g, 6.0 mmol), Compound 2-4B (2.4 g, 6.6
mmol), Pd.sub.2(dba).sub.3 (0.3 g, 0.3 mmol) and toluene (50 ml)
were put into a 250 ml reaction vessel in a dry box. The reaction
vessel was removed from the dry box, and then sodium carbonate
anhydrous (2M, 20 ml) was added into the solution. The reactants
were stirred and heated at 90.degree. C. overnight. The reaction
was monitored by HPLC. After the solution was cooled to RT, an
organic layer was separated. An aqueous layer was washed with
dichloromethane and the organic layer was concentrated with rotary
evaporation to obtain a gray powder. The gray powder was purified
with alumina, precipitated with hexane, and purified with
silica-gel column chromatography to give Compound 2-4 (2.0 g,
yield: 67%) of white powder.
Synthesis Example 13: Synthesis of Compound 2-5
##STR00062##
[0246] Compound 2-5A (2.0 g, 5.2 mmol), Compound 2-5B (2.0 g, 5.7
mmol), Pd.sub.2(dba).sub.3 (0.24 g, 0.26 mmol) and toluene (50 ml)
were put into a 250 ml reaction vessel in a dry box. The reaction
vessel was removed from the dry box, and then sodium carbonate
anhydrous (2M, 20 ml) was added into the solution. The reactants
were stirred and heated at 90.degree. C. overnight. The reaction
was monitored by HPLC. After the solution was cooled to RT, an
organic layer was separated. An aqueous layer was washed with
dichloromethane and the organic layer was concentrated with rotary
evaporation to obtain a gray powder. The gray powder was purified
with alumina, precipitated with hexane, and purified with
silica-gel column chromatography to give Compound 2-5 (2.0 g,
yield: 81%) of white powder.
Synthesis Example 14: Synthesis of Compound 2-6
##STR00063##
[0248] Compound 2-6A (2.0 g, 5.2 mmol), Compound 2-6B (2.0 g, 5.7
mmol), Pd.sub.2(dba).sub.3 (0.24 g, 0.26 mmol) and toluene (50 ml)
were put into a 250 ml reaction vessel in a dry box. The reaction
vessel was removed from the dry box, and then sodium carbonate
anhydrous (2M, 20 ml) was added into the solution. The reactants
were stirred and heated at 90.degree. C. overnight. The reaction
was monitored by HPLC. After the solution was cooled to RT, an
organic layer was separated. An aqueous layer was washed with
dichloromethane and the organic layer was concentrated with rotary
evaporation to obtain a gray powder. The gray powder was purified
with alumina, precipitated with hexane, and purified with
silica-gel column chromatography to give Compound 2-6 (2.0 g,
yield: 81%) of white powder.
Synthesis Example 15: Synthesis of Compound 2-7
##STR00064##
[0250] Aluminum chloride (0.5 g, 3.6 mmol) was added into a
solution of Compound 2-1 (5.0 g, 9.9 mmol) dissolved in
perdeuterobenzene (100 ml) under nitrogen atmosphere. Obtained
mixture was stirred at RT for 6 hours, and then D.sub.2O (50 ml)
was added into the mixture. After an organic layer was separated
from an aqueous layer, the aqueous layer was washed with
dichloromethane (30 ml). The obtained organic layer was dried with
MgSO.sub.4 and volatile components were removed by rotary
evaporation. A crude product was purified with column
chromatography to give Compound 2-7 (4.5 g, yield: 85%) of white
powder.
Synthesis Example 16: Synthesis of Compound 2-8
##STR00065##
[0252] Aluminum chloride (0.9 g, 4.3 mmol) was added into a
solution of Compound 2-2 (5.0 g, 11.6 mmol) dissolved in
perdeuterobenzene (120 ml) under nitrogen atmosphere. Obtained
mixture was stirred at RT for 6 hours, and then D.sub.2O (70 ml)
was added into the mixture. After an organic layer was separated
from an aqueous layer, the aqueous layer was washed with
dichloromethane (50 ml). The obtained organic layer was dried with
MgSO.sub.4 and volatile components were removed by rotary
evaporation. A crude product was purified with column
chromatography to give Compound 2-8 (4.0 g, yield: 76%) of white
powder.
Synthesis Example 17: Synthesis of Compound 2-9
##STR00066##
[0254] Aluminum chloride (0.9 g, 4.3 mmol) was added into a
solution of Compound 2-3 (5.0 g, 11.9 mmol) dissolved in
perdeuterobenzene (120 ml) under nitrogen atmosphere. Obtained
mixture was stirred at RT for 6 hours, and then D.sub.2O (70 ml)
was added into the mixture. After an organic layer was separated
from an aqueous layer, the aqueous layer was washed with
dichloromethane (50 ml). The obtained organic layer was dried with
MgSO.sub.4 and volatile components were removed by rotary
evaporation. A crude product was purified with column
chromatography to give Compound 2-9 (3.0 g, yield: 57%) of white
powder.
Synthesis Example 18: Synthesis of Compound 2-10
##STR00067##
[0256] Aluminum chloride (0.9 g, 4.3 mmol) was added into a
solution of Compound 2-4 (5.0 g, 10.1 mmol) dissolved in
perdeuterobenzene (120 ml) under nitrogen atmosphere. Obtained
mixture was stirred at RT for 6 hours, and then D.sub.2O (70 ml)
was added into the mixture. After an organic layer was separated
from an aqueous layer, the aqueous layer was washed with
dichloromethane (50 ml). The obtained organic layer was dried with
MgSO.sub.4 and volatile components were removed by rotary
evaporation. A crude product was purified with column
chromatography to give Compound 2-10 (3.5 g, yield: 67%) of white
powder.
Synthesis Example 19: Synthesis of Compound 2-11
##STR00068##
[0258] Aluminum chloride (0.9 g, 4.3 mmol) was added into a
solution of Compound 2-5 (5.0 g, 10.6 mmol) dissolved in
perdeuterobenzene (120 ml) under nitrogen atmosphere. Obtained
mixture was stirred at RT for 6 hours, and then D.sub.2O (70 ml)
was added into the mixture. After an organic layer was separated
from an aqueous layer, the aqueous layer was washed with
dichloromethane (50 ml). The obtained organic layer was dried with
MgSO.sub.4 and volatile components were removed by rotary
evaporation. A crude product was purified with column
chromatography to give Compound 2-11 (4.0 g, yield: 77%) of white
powder.
Synthesis Example 20: Synthesis of Compound 2-12
##STR00069##
[0260] Aluminum chloride (0.9 g, 4.3 mmol) was added into a
solution of Compound 2-6 (5.0 g, 10.6 mmol) dissolved in
perdeuterobenzene (120 ml) under nitrogen atmosphere. Obtained
mixture was stirred at RT for 6 hours, and then D.sub.2O (70 ml)
was added into the mixture. After an organic layer was separated
from an aqueous layer, the aqueous layer was washed with
dichloromethane (50 ml). The obtained organic layer was dried with
MgSO.sub.4 and volatile components were removed by rotary
evaporation. A crude product was purified with column
chromatography to give Compound 2-12 (4.3 g, yield: 82%) of white
powder.
Fabrication of Organic Light Emitting Diode (OLED) 1
[0261] A glass substrate (40 mm.times.40 mm.times.0.5 mm) onto
which ITO was coated as a thin film was washed and ultrasonically
cleaned by solvent such as isopropyl alcohol, acetone and distilled
water for 5 minutes and dried at 100.degree. C. oven. After
cleaning the substrate, the substrate was treated with O.sub.2
plasma under vacuum for 2 minutes and then transferred to a vacuum
chamber for depositing emission layer. Subsequently, an emissive
layer and a cathode were deposited by evaporation from a heating
boat under about 5.about.7.times.10.sup.-7 Torr with a deposition
rate of 1 .ANG./s as the following order:
[0262] An HIL (Formula 11 (97 wt %) and Formula 12 (3 wt %), 100
.ANG.); an HTL (Formula 11, 100 .ANG.); an EBL (H23 in Formula 6,
100 .ANG.); an EML (Host (H, 98 wt %) and Dopant (D, 2 wt %), 200
.ANG.); an HBL (E1 in Formula 8, 100 .ANG.); an EIL (Formula 13 (98
wt %), Li (2 wt %), 200 .ANG.); and a cathode (Al, 500 .ANG.).
[0263] And then, the OLED was encapsulated with UV-curable epoxy
and moisture getter.
Comparative Examples 1-8 (Ref.1-8): Fabrication of OLED
[0264] An OLED where the EML includes Compound 2-1 as a host and
each of Compound 1-1 (Ref.1), Compound 1-4 (Ref.2), Compound 1-6
(Ref.3), Compound 1-8 (Ref.4), Compound 1-11 (Ref.5), Compound 1-12
(Ref.6), Compound 1-13 (Ref.7) and Compound 1-17 (Ref.8) in Formula
3 as a dopant, respectively, was fabricated.
Comparative Examples 9-16 (Ref.9-16): Fabrication of OLED
[0265] An OLED where the EML includes Compound 2-2 as a host and
each of Compound 1-1 (Ref.9), Compound 1-4 (Ref.10), Compound 1-6
(Ref.11), Compound 1-8 (Ref.12), Compound 1-11 (Ref.13), Compound
1-12 (Ref.14), Compound 1-13 (Ref.15) and Compound 1-17 (Ref.18) in
Formula 3 as a dopant, respectively, was fabricated.
Experimental Example 1: Measurement of Luminous Properties of
OLEDs
[0266] Each of the OLEDs, having 9 mm.sup.2 of emission area,
fabricated in Comparative Examples 1 to 16 connected to an external
power source and then luminous properties for all the OLEDs were
evaluated using a constant current source (KEITHILEY) and a
photometer PR650 at room temperature. In particular, driving
voltage (V), current efficiency (cd/A) and CIE color coordinates at
a current density of 10 mA/cm.sup.2 and time period (T.sub.95) at
which the luminance was reduced to 95% from initial luminance at
40.degree. C. and at a current density of 22.5 mA/m.sup.2. The
measurement results are indicated in the following Table 1.
TABLE-US-00001 TABLE 1 Luminous Properties of OLED Sample Dopant
Host V EQE (%) CIE(x,y) T.sub.95 (hr) Ref. 1 1-1 2-1 3.99 6.35
(0.140, 0.061) 63 Ref. 2 1-4 2-1 3.94 6.33 (0.131, 0.089) 68 Ref. 3
1-6 2-1 3.90 6.61 (0.139, 0.074) 88 Ref. 4 1-8 2-1 3.88 6.63
(0.137, 0.079) 82 Ref. 5 1-11 2-1 3.89 6.61 (0.140, 0.074) 101 Ref.
6 1-12 2-1 3.90 6.59 (0.140, 0.073) 95 Ref. 7 1-13 2-1 3.91 6.64
(0.137, 0.080) 94 Ref. 8 1-17 2-1 3.91 6.58 (0.137, 0.079) 89 Ref.
9 1-1 2-2 4.20 6.24 (0.140, 0.060) 69 Ref. 10 1-4 2-2 4.20 6.22
(0.131, 0.090) 74 Ref. 11 1-6 2-2 4.15 6.49 (0.138, 0.074) 96 Ref.
12 1-8 2-2 4.19 6.51 (0.137, 0.079) 106 Ref. 13 1-11 2-2 4.20 6.50
(0.140, 0.074) 110 Ref. 14 1-12 2-2 4.21 6.47 (0.141, 0.074) 103
Ref. 15 1-13 2-2 4.20 6.53 (0.138, 0.080) 102 Ref. 16 1-17 2-2 4.19
6.47 (0.137, 0.079) 96
Comparative Examples 17-24 (Ref.17-24): Fabrication of OLED
[0267] An OLED where the EML includes Compound 2-3 as a host and
Compound 1-1 (Ref.17), Compound 1-4 (Ref.18), Compound 1-6
(Ref.19), Compound 1-8 (Ref.20), Compound 1-11 (Ref.21), Compound
1-12 (Ref.22), Compound 1-13 (Ref.23) and Compound 1-17 (Ref.24) in
Formula 3 as a dopant, respectively, was fabricated.
Comparative Examples 25-32 (Ref.25-32): Fabrication of OLED
[0268] An OLED where the EML includes Compound 2-4 as a host and
Compound 1-1 (Ref.25), Compound 1-4 (Ref.26), Compound 1-6
(Ref.27), Compound 1-8 (Ref.28), Compound 1-11 (Ref.29), Compound
1-12 (Ref.30), Compound 1-13 (Ref.31) and Compound 1-17 (Ref.32) in
Formula 3 as a dopant, respectively, was fabricated.
Experimental Example 2: Measurement of Luminous Properties of
OLEDs
[0269] Luminous properties for each of the OLEDs fabricated in
Comparative Examples 17-32 were measured using the same procedure
as in Experimental Example 1. The measurement results are indicated
in the following Table 2.
TABLE-US-00002 TABLE 2 Luminous Properties of OLEDs Sample Dopant
Host V EQE (%) CIE(x,y) T.sub.95 (hr) Ref. 17 1-1 2-3 3.80 6.21
(0.140, 0.063) 56 Ref. 18 1-4 2-3 3.79 6.17 (0.130, 0.092) 61 Ref.
19 1-6 2-3 3.80 6.45 (0.139, 0.076) 79 Ref. 20 1-8 2-3 3.78 6.47
(0.138, 0.081) 73 Ref. 21 1-11 2-3 3.78 6.46 (0.141, 0.075) 90 Ref.
22 1-12 2-3 3.78 6.44 (0.141, 0.075) 85 Ref. 23 1-13 2-3 3.80 6.49
(0.136, 0.081) 84 Ref. 24 1-17 2-3 3.79 6.42 (0.136, 0.081) 79 Ref.
25 1-1 2-4 3.80 6.22 (0.139, 0.062) 56 Ref. 26 1-4 2-4 3.79 6.20
(0.131, 0.092) 60 Ref. 27 1-6 2-4 3.80 6.43 (0.137, 0.081) 80 Ref.
28 1-8 2-4 3.79 6.42 (0.136, 0.084) 73 Ref. 29 1-11 2-4 3.81 6.47
(0.139, 0.076) 91 Ref. 30 1-12 2-4 3.80 6.44 (0.139, 0.077) 84 Ref.
31 1-13 2-4 3.79 6.50 (0.136, 0.084) 83 Ref. 32 1-17 2-4 3.80 6.43
(0.135, 0.087) 80
Comparative Examples 33-40 (Ref.33-40): Fabrication of OLED
[0270] An OLED where the EML includes Compound 2-5 as a host and
Compound 1-1 (Ref.33), Compound 1-4 (Ref.34), Compound 1-6
(Ref.35), Compound 1-8 (Ref.36), Compound 1-11 (Ref.37), Compound
1-12 (Ref.38), Compound 1-13 (Ref.39) and Compound 1-17 (Ref.40) in
Formula 3 as a dopant, respectively, was fabricated.
Comparative Examples 41-48 (Ref.41-48): Fabrication of OLED
[0271] An OLED where the EML includes Compound 2-6 as a host and
Compound 1-1 (Ref.41), Compound 1-4 (Ref.42), Compound 1-6
(Ref.43), Compound 1-8 (Ref.44), Compound 1-11 (Ref.45), Compound
1-12 (Ref.46), Compound 1-13 (Ref.47) and Compound 1-17 (Ref.48) in
Formula 3 as a dopant, respectively, was fabricated.
Experimental Example 3: Measurement of Luminous Properties of
OLEDs
[0272] Luminous properties for each of the OLEDs fabricated in
Comparative Examples 33-48 were measured using the same procedure
as in Experimental Example 1. The measurement results are indicated
in the following Table 3.
TABLE-US-00003 TABLE 3 Luminous Properties of OLEDs Sample Dopant
Host V EQE (%) CIE(x,y) T.sub.95 (hr) Ref. 33 1-1 2-5 3.65 6.15
(0.140, 0.064) 51 Ref. 34 1-4 2-5 3.61 6.12 (0.130, 0.094) 55 Ref.
35 1-6 2-5 3.62 6.10 (0.138, 0.082) 75 Ref. 36 1-8 2-5 3.60 6.12
(0.138, 0.085) 68 Ref. 37 1-11 2-5 3.62 6.10 (0.141, 0.080) 86 Ref.
38 1-12 2-5 3.63 6.15 (0.141, 0.080) 79 Ref. 39 1-13 2-5 3.62 6.15
(0.136, 0.085) 78 Ref. 40 1-17 2-5 3.63 6.16 (0.136, 0.088) 75 Ref.
41 1-1 2-6 3.65 6.16 (0.140, 0.064) 50 Ref. 42 1-4 2-6 3.60 6.13
(0.130, 0.094) 54 Ref. 43 1-6 2-6 3.61 6.11 (0.138, 0.082) 76 Ref.
44 1-8 2-6 3.59 6.11 (0.138, 0.085) 69 Ref. 45 1-11 2-6 3.61 6.11
(0.141, 0.080) 85 Ref. 46 1-12 2-6 3.62 6.14 (0.141, 0.080) 80 Ref.
47 1-13 2-6 3.61 6.14 (0.136, 0.085) 79 Ref. 48 1-17 2-6 3.62 6.15
(0.136, 0.088) 76
Examples 1-8 (Ex.1-8): Fabrication of OLED
[0273] An OLED where the EML includes Compound 2-7 as a host and
Compound 1-1 (Ex.1), Compound 1-4 (Ex.2), Compound 1-6 (Ex.3),
Compound 1-8 (Ex.4), Compound 1-11 (Ex.5), Compound 1-12 (Ex.6),
Compound 1-13 (Ex.7) and Compound 1-17 (Ex.8) in Formula 3 as a
dopant, respectively, was fabricated.
Examples 9-16 (Ref.9-16): Fabrication of OLED
[0274] An OLED where the EML includes Compound 2-8 as a host and
Compound 1-1 (Ex.9), Compound 1-4 (Ex.10), Compound 1-6 (Ex.11),
Compound 1-8 (Ex.12), Compound 1-11 (Ex.13), Compound 1-12 (Ex.14),
Compound 1-13 (Ex.15) and Compound 1-17 (Ex.16) in Formula 3 as a
dopant, respectively, was fabricated.
Experimental Example 4: Measurement of Luminous Properties of
OLEDs
[0275] Luminous properties for each of the OLEDs fabricated in
Examples 1-16 were measured using the same procedure as in
Experimental Example 1. The measurement results are indicated in
the following Table 4.
TABLE-US-00004 TABLE 4 Luminous Properties of OLEDs Sample Dopant
Host V EQE (%) CIE(x,y) T.sub.95 (hr) Ex. 1 1-1 2-7 3.98 6.28
(0.140, 0.060) 95 Ex. 2 1-4 2-7 3.95 6.30 (0.131, 0.089) 102 Ex. 3
1-6 2-7 3.91 6.57 (0.140, 0.074) 133 Ex. 4 1-8 2-7 3.88 6.59
(0.137, 0.080) 123 Ex. 5 1-11 2-7 3.89 6.60 (0.139, 0.074) 151 Ex.
6 1-12 2-7 3.89 6.54 (0.140, 0.072) 142 Ex. 7 1-13 2-7 3.90 6.62
(0.137, 0.079) 141 Ex. 8 1-17 2-7 3.91 6.55 (0.137, 0.079) 133 Ex.
9 1-1 2-8 4.21 6.19 (0.140, 0.061) 103 Ex. 10 1-4 2-8 4.20 6.20
(0.131, 0.089) 111 Ex. 11 1-6 2-8 4.16 6.47 (0.139, 0.074) 144 Ex.
12 1-8 2-8 4.20 6.48 (0.137, 0.078) 159 Ex. 13 1-11 2-8 4.20 6.45
(0.140, 0.074) 165 Ex. 14 1-12 2-8 4.20 6.32 (0.141, 0.073) 154 Ex.
15 1-13 2-8 4.19 6.51 (0.138, 0.079) 153 Ex. 16 1-17 2-8 4.20 6.33
(0.137, 0.078) 144
Examples 17-24 (Ex.17-24): Fabrication of OLED
[0276] An OLED where the EML includes Compound 2-9 as a host and
Compound 1-1 (Ex.17), Compound 1-4 (Ex.18), Compound 1-6 (Ex.19),
Compound 1-8 (Ex.20), Compound 1-11 (Ex.21), Compound 1-12 (Ex.22),
Compound 1-13 (Ex.23) and Compound 1-17 (Ex.24) in Formula 3 as a
dopant, respectively, was fabricated.
Examples 25-32 (Ref.25-32): Fabrication of OLED
[0277] An OLED where the EML includes Compound 2-10 as a host and
Compound 1-1 (Ex.25), Compound 1-4 (Ex.26), Compound 1-6 (Ex.27),
Compound 1-8 (Ex.28), Compound 1-11 (Ex.29), Compound 1-12 (Ex.30),
Compound 1-13 (Ex.31) and Compound 1-17 (Ex.32) in Formula 3 as a
dopant, respectively, was fabricated.
Experimental Example 5: Measurement of Luminous Properties of
OLEDs
[0278] Luminous properties for each of the OLEDs fabricated in
Examples 17-32 were measured using the same procedure as in
Experimental Example 1. The measurement results are indicated in
the following Table 5.
TABLE-US-00005 TABLE 5 Luminous Properties of OLEDs Sample Dopant
Host V EQE (%) CIE(x,y) T.sub.95 (hr) Ex. 17 1-1 2-9 3.81 6.21
(0.139, 0.062) 84 Ex. 18 1-4 2-9 3.80 6.19 (0.131, 0.092) 90 Ex. 19
1-6 2-9 3.79 6.42 (0.137, 0.081) 120 Ex. 20 1-8 2-9 3.78 6.41
(0.136, 0.084) 109 Ex. 21 1-11 2-9 3.80 6.45 (0.139, 0.076) 136 Ex.
22 1-12 2-9 3.81 6.42 (0.139, 0.077) 126 Ex. 23 1-13 2-9 3.80 6.49
(0.136, 0.084) 124 Ex. 24 1-17 2-9 3.80 6.41 (0.135, 0.087) 120 Ex.
25 1-1 2-10 3.80 6.21 (0.139, 0.062) 84 Ex. 26 1-4 2-10 3.79 6.22
(0.131, 0.092) 90 Ex. 27 1-6 2-10 3.80 6.42 (0.137, 0.081) 120 Ex.
28 1-8 2-10 3.79 6.41 (0.136, 0.084) 109 Ex. 29 1-11 2-10 3.81 6.45
(0.139, 0.076) 136 Ex. 30 1-12 2-10 3.80 6.45 (0.139, 0.077) 126
Ex. 31 1-13 2-10 3.79 6.49 (0.136, 0.084) 124 Ex. 32 1-17 2-10 3.80
6.42 (0.135, 0.087) 120
Examples 33-40 (Ex.33-40): Fabrication of OLED
[0279] An OLED where the EML includes Compound 2-11 as a host and
Compound 1-1 (Ex.33), Compound 1-4 (Ex.34), Compound 1-6 (Ex.35),
Compound 1-8 (Ex.36), Compound 1-11 (Ex.37), Compound 1-12 (Ex.38),
Compound 1-13 (Ex.39) and Compound 1-17 (Ex.40) in Formula 3 as a
dopant, respectively, was fabricated.
Examples 41-48 (Ref.41-48): Fabrication of OLED
[0280] An OLED where the EML includes Compound 2-12 as a host and
Compound 1-1 (Ex.41), Compound 1-4 (Ex.42), Compound 1-6 (Ex.43),
Compound 1-8 (Ex.44), Compound 1-11 (Ex.45), Compound 1-12 (Ex.46),
Compound 1-13 (Ex.47) and Compound 1-17 (Ex.48) in Formula 3 as a
dopant, respectively, was fabricated.
Experimental Example 6: Measurement of Luminous Properties of
OLEDs
[0281] Luminous properties for each of the OLEDs fabricated in
Examples 33-48 were measured using the same procedure as in
Experimental Example 1. The measurement results are indicated in
the following Table 6.
TABLE-US-00006 TABLE 6 Luminous Properties of OLEDs Sample Dopant
Host V EQE (%) CIE(x,y) T.sub.95 (hr) Ex. 33 1-1 2-11 3.64 6.14
(0.140, 0.064) 76 Ex. 34 1-4 2-11 3.62 6.11 (0.130, 0.094) 82 Ex.
35 1-6 2-11 3.61 6.09 (0.138, 0.082) 112 Ex. 36 1-8 2-11 3.61 6.11
(0.138, 0.085) 102 Ex. 37 1-11 2-11 3.61 6.11 (0.141, 0.080) 129
Ex. 38 1-12 2-11 3.62 6.14 (0.141, 0.080) 119 Ex. 39 1-13 2-11 3.63
6.13 (0.136, 0.085) 117 Ex. 40 1-17 2-11 3.64 6.15 (0.136, 0.088)
112 Ex. 41 1-1 2-12 3.64 6.15 (0.140, 0.064) 75 Ex. 42 1-4 2-12
3.61 6.14 (0.130, 0.094) 81 Ex. 43 1-6 2-12 3.60 6.12 (0.138,
0.082) 114 Ex. 44 1-8 2-12 3.58 6.12 (0.138, 0.085) 103 Ex. 45 1-11
2-12 3.60 6.12 (0.141, 0.080) 127 Ex. 46 1-12 2-12 3.61 6.13
(0.141, 0.080) 120 Ex. 47 1-13 2-12 3.60 6.15 (0.136, 0.085) 118
Ex. 48 1-17 2-12 3.61 6.14 (0.136, 0.088) 114
[0282] Summarizing the results in Tables 1 to 6, compared to the
OLEDs fabricated in Ref.1 to Ref.48 where the EML includes a
non-deuterated anthracene-based compound (Compounds 2-1 to Compound
2-6) as the host, the OLEDs fabricated in Ex.1 to Ex.48 where the
EML includes a deuterated anthracene-based compound (Compounds 2-7
to Compound 2-12) as the host improved their luminous efficiency
and luminous lifespan.
[0283] In addition, compared to the OLEDs fabricated in Ex.17-48,
the OLEDs fabricated in Ex.1-8 where the EML includes the Compound
2-7 as the host and the OLEDs fabricated in Ex. 9-16 wherein the
EML includes the Compound 2-9 as the host improved their luminous
efficiency and luminous lifespan. In other words, when the
anthracene-based compound, where a naphthyl moiety (1-naphthyl) is
linked directly to one side of an anthracene moiety and other
naphthyl moiety (2-naphthyl) is linked directly or via a bridging
group (linker) to the other side of the anthracene moiety and is
deuterated, are used as the host in the EML, the luminous
efficiency and the luminous lifespan of the OLEDs are further
increased.
[0284] Also, compared to the OLEDs fabricated in Ex.1-8 where the
EML includes the Compound 2-7 as the host, the OLEDs fabricated in
Ex.9-16 where the EML includes the Compound 2-8 as the host showed
sufficient luminous lifespan. On the contrary, the OLEDs where the
EML includes the Compound 2-7 as the host lowered their driving
voltages. In other words, the OLEDs where the EML includes the
anthracene-based compound, where a naphthyl moiety (1-naphthyl) is
linked to directly to one side of the anthracene moiety and the
other naphthyl moiety (2-naphthyl) is linked directly or via the
bridging group and is deuterated, lowered its driving voltage and
improved their luminous efficiency and luminous lifespan.
[0285] Also, compared to the OLEDs where the EML includes the
boron-based compound having symmetrical chemical structure
(Compounds 1-1 and 1-4) as the dopant, the OLEDs where the EML
includes the boron-based compound having asymmetrical chemical
structure (Compounds 1-6 and 1-8) as the dopant improved their
luminous efficiency and luminous lifespan.
[0286] In addition, the OLEDs where the EML includes the
boron-based compound which is deuterated and having the asymmetric
structure (Compounds, 1-11, 1-12, 1-13 and 1-17) as the dopant
enhanced their luminous efficiency and luminous lifespan further.
Particularly, when the HIL and the HTL includes the compound in
Formula 11 and the EBL includes the amine-based compound of Formula
5, the OLED can improve its luminous properties.
Fabrication of Organic Light Emitting Diode (OLED) 2
[0287] A glass substrate (40 mm.times.40 mm.times.0.5 mm) onto
which ITO was coated as a thin film was washed and ultrasonically
cleaned by solvent such as isopropyl alcohol, acetone and distilled
water for 5 minutes and dried at 100.degree. C. oven. After
cleaning the substrate, the substrate was treated with O.sub.2
plasma under vacuum for 2 minutes and then transferred to a vacuum
chamber for depositing emission layer. Subsequently, an emissive
layer and a cathode were deposited by evaporation from a heating
boat under about 5.about.7.times.10.sup.-7 Torr with a deposition
rate of 1 .LAMBDA./s as the following order:
[0288] An HIL (Formula 11 (97 wt %) and Formula 12 (3 wt %), 100
.ANG.); an HTL (Formula 11, 100 .ANG.); an EBL (100 .ANG.); an EML
(Host (H, 98 wt %) and Dopant (D, 2 wt %), 200 .ANG.); an HBL (100
.ANG.); an EIL (Formula 13 (98 wt %), Li (2 wt %), 200 .ANG.); and
a cathode (Al, 500 .ANG.).
[0289] And then, the OLED was encapsulated with UV-curable epoxy
and moisture getter.
Comparative Example 49 (Ref.49): Fabrication of OLED
[0290] An OLED where the EBL includes the following Ref.EBL, the
EML includes Compound 1-1 (dopant) in Formula 2 and Compound 2-1
(host) and the HBL includes the following Ref.HBL was
fabricated.
Examples 49-56 (Ex.49-56): Fabrication of OLEDs
[0291] An OLED where the EML includes the Compound 1-1 (dopant) in
Formula 2 and Compound 2-7 (host) in Formula 4, the EBL includes
the following Ref.EBL (Ex.49-51), H4 in Formula 6 (Ex.52-54) or H3
in Formula 6 (Ex.55-57), and the HBL includes the following Ref.HBL
(Ex.49, 52 and 55), E1 in Formula 8 (Ex.50, 53 and 56) or F1 in
Formula 10 (Ex.51, 54 and 57), respectively, were fabricated.
##STR00070##
Experimental Example 7: Measurement of Luminous Properties of
OLEDs
[0292] Luminous properties for each of the OLEDs fabricated in
Examples 49-57 and Comparative Example 49 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 7.
TABLE-US-00007 TABLE 7 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 49 Ref. 1-1 2-1 Ref.
4.00 3.00 0.140 0.063 22 Ex. 49 Ref. 1-1 2-7 Ref. 4.02 2.97 0.140
0.062 30 Ex. 50 Ref. 1-1 2-7 E1 4.01 2.99 0.140 0.061 38 Ex. 51
Ref. 1-1 2-7 F1 3.96 3.04 0.140 0.060 46 Ex. 52 H4 1-1 2-7 Ref.
4.01 5.85 0.139 0.060 87 Ex. 53 H4 1-1 2-7 E1 3.98 5.99 0.140 0.060
115 Ex. 54 H4 1-1 2-7 F1 3.98 6.17 0.140 0.060 133 Ex. 55 H3 1-1
2-7 Ref. 4.01 6.20 0.139 0.62 85 Ex. 56 H3 1-1 2-7 E1 4.00 6.31
0.141 0.059 114 Ex. 57 H3 1-1 2-7 F1 3.96 6.48 0.141 0.060 124
Comparative Example 50 (Ref.50): Fabrication of OLED
[0293] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-1 (dopant) in Formula 2 and Compound 2-3 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples 58-66 (Ex.58-66): Fabrication of OLEDs
[0294] An OLED where the EML includes the Compound 1-1 (dopant) in
Formula 2 and Compound 2-9 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.58-60), H4 in Formula 6 (Ex.61-63) or H3 in Formula
6 (Ex.64-66), respectively, and the HBL includes the Ref.HBL
(Ex.58, 61 and 64), E1 in Formula 8 (Ex.59, 62 and 65) or F1 in
Formula 10 (Ex.60, 63 and 66), respectively, were fabricated.
Experimental Example 8: Measurement of Luminous Properties of
OLEDs
[0295] Luminous properties for each of the OLEDs fabricated in
Examples 58-66 and Comparative Example 50 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 8.
TABLE-US-00008 TABLE 8 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref 50 Ref. 1-1 2-3 Ref.
3.86 2.92 0.139 0.064 21 Ex. 58 Ref. 1-1 2-9 Ref. 3.87 2.93 0.140
0.063 28 Ex. 59 Ref. 1-1 2-9 E1 3.83 2.98 0.139 0.062 36 Ex. 60
Ref. 1-1 2-9 F1 3.90 3.08 0.141 0.062 39 Ex. 61 H4 1-1 2-9 Ref.
3.86 5.81 0.140 0.063 83 Ex. 62 H4 1-1 2-9 E1 3.81 5.93 0.139 0.062
102 Ex. 63 H4 1-1 2-9 F1 3.90 6.11 0.140 0.063 116 Ex. 64 H3 1-1
2-9 Ref. 3.89 6.15 0.139 0.064 79 Ex. 65 H3 1-1 2-9 E1 3.82 6.22
0.139 0.062 97 Ex. 66 H3 1-1 2-9 F1 3.89 6.41 0.140 0.061 115
Comparative Example 51 (Ref.51): Fabrication of OLED
[0296] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-4 (dopant) in Formula 2 and Compound 2-1 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples 67-75 (Ex.67-75): Fabrication of OLEDs
[0297] An OLED where the EML includes the Compound 1-4 (dopant) in
Formula 2 and Compound 2-7 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.67-69), H4 in Formula 6 (Ex.70-72) or H3 in Formula
6 (Ex.73-75), respectively, and the HBL includes the Ref.HBL
(Ex.67, 70 and 73), E1 in Formula 8 (Ex.68, 71 and 74) or F1 in
Formula 10 (Ex.69, 72 and 75), respectively, were fabricated.
Experimental Example 9: Measurement of Luminous Properties of
OLEDs
[0298] Luminous properties for each of the OLEDs fabricated in
Examples 67-75 and Comparative Example 51 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 9.
TABLE-US-00009 TABLE 9 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 51 Ref. 1-4 2-1 Ref.
3.99 2.95 0.132 0.062 23 Ex. 67 Ref. 1-4 2-7 Ref. 4.00 2.96 0.131
0.091 34 Ex. 68 Ref. 1-4 2-7 E1 3.92 3.01 0.132 0.090 44 Ex. 69
Ref. 1-4 2-7 F1 3.92 3.10 0.130 0.090 49 Ex. 70 H4 1-4 2-7 Ref.
3.99 5.88 0.131 0.090 92 Ex. 71 H4 1-4 2-7 E1 3.95 6.01 0.131 0.089
123 Ex. 72 H4 1-4 2-7 F1 3.95 6.19 0.130 0.090 148 Ex. 73 H3 1-4
2-7 Ref. 3.95 6.18 0.131 0.090 88 Ex. 74 H3 1-4 2-7 E1 3.97 6.31
0.130 0.090 121 Ex. 75 H3 1-4 2-7 F1 3.92 6.55 0.130 0.089 138
Comparative Example 52 (Ref.52): Fabrication of OLED
[0299] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-4 (dopant) in Formula 2 and Compound 2-3 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples 76-84 (Ex.76-84): Fabrication of OLEDs
[0300] An OLED where the EML includes the Compound 1-4 (dopant) in
Formula 2 and Compound 2-9 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.76-78), H4 in Formula 6 (Ex.79-81) or H3 in Formula
6 (Ex.82-84), respectively, and the HBL includes the Ref.HBL
(Ex.76, 79 and 82), E1 in Formula 8 (Ex.77, 80 and 83) or F1 in
Formula 10 (Ex.78, 81 and 84), respectively, were fabricated.
Experimental Example 10: Measurement of Luminous Properties of
OLEDs
[0301] Luminous properties for each of the OLEDs fabricated in
Examples 76-84 and Comparative Example 52 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 10.
TABLE-US-00010 TABLE 10 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 52 Ref. 1-4 2-3 Ref.
3.82 2.89 0.131 0.092 20 Ex. 76 Ref. 1-4 2-9 Ref. 3.87 2.89 0.131
0.092 29 Ex. 77 Ref. 1-4 2-9 E1 3.80 2.97 0.131 0.091 36 Ex. 78
Ref. 1-4 2-9 F1 3.87 3.08 0.132 0.091 44 Ex. 79 H4 1-4 2-9 Ref.
3.85 5.77 0.130 0.092 84 Ex. 80 H4 1-4 2-9 E1 3.80 5.91 0.131 0.092
109 Ex. 81 H4 1-4 2-9 F1 3.82 6.09 0.131 0.091 133 Ex. 82 H3 1-4
2-9 Ref. 3.85 6.09 0.131 0.091 83 Ex. 83 H3 1-4 2-9 E1 3.77 6.23
0.131 0.092 110 Ex. 84 H3 1-4 2-9 F1 3.85 6.39 0.130 0.092 131
Comparative Example 53 (Ref.53): Fabrication of OLED
[0302] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-6 (dopant) in Formula 2 and Compound 2-1 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples 85-93 (Ex.85-93): Fabrication of OLEDs
[0303] An OLED where the EML includes the Compound 1-6 (dopant) in
Formula 2 and Compound 2-7 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.85-87), H4 in Formula 6 (Ex.88-90) or H3 in Formula
6 (Ex.91-93), respectively, and the HBL includes the Ref.HBL
(Ex.85, 88 and 91), E1 in Formula 8 (Ex.86, 89 and 92) or F1 in
Formula 10 (Ex.87, 90 and 93), respectively, were fabricated.
Experimental Example 11: Measurement of Luminous Properties of
OLEDs
[0304] Luminous properties for each of the OLEDs fabricated in
Examples 85-93 and Comparative Example 53 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 11.
TABLE-US-00011 TABLE 11 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 53 Ref. 1-6 2-1 Ref.
3.93 3.11 0.140 0.076 26 Ex. 85 Ref. 1-6 2-7 Ref. 3.95 3.09 0.140
0.075 45 Ex. 86 Ref. 1-6 2-7 E1 3.95 3.14 0.141 0.074 54 Ex. 87
Ref. 1-6 2-7 F1 3.91 3.19 0.140 0.075 61 Ex. 88 H4 1-6 2-7 Ref.
3.96 6.13 0.140 0.076 122 Ex. 89 H4 1-6 2-7 E1 3.91 6.27 0.140
0.074 161 Ex. 90 H4 1-6 2-7 F1 3.91 6.38 0.140 0.074 190 Ex. 91 H3
1-6 2-7 Ref. 3.93 6.45 0.139 0.077 110 Ex. 92 H3 1-6 2-7 E1 3.92
6.58 0.140 0.074 150 Ex. 93 H3 1-6 2-7 F1 3.92 6.70 0.140 0.074
177
Comparative Example 54 (Ref.54): Fabrication of OLED
[0305] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-6 (dopant) in Formula 2 and Compound 2-3 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples: 94-102 (Ex.94-102): Fabrication of OLEDs
[0306] An OLED where the EML includes the Compound 1-6 (dopant) in
Formula 2 and Compound 2-9 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.94-96), H4 in Formula 6 (Ex.97-99) or H3 in Formula
6 (Ex.100-102), respectively, and the HBL includes the Ref.HBL
(Ex.94, 97 and 100), E1 in Formula 8 (Ex.95, 98 and 101) or F1 in
Formula 10 (Ex.96, 99 and 102), respectively, were fabricated.
Experimental Example 12: Measurement of Luminous Properties of
OLEDs
[0307] Luminous properties for each of the OLEDs fabricated in
Examples 94-102 and Comparative Example 54 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 12.
TABLE-US-00012 TABLE 12 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 54 Ref. 1-6 2-3 Ref.
3.82 3.01 0.139 0.076 28 Ex. 94 Ref. 1-6 2-9 Ref. 3.84 3.03 0.138
0.081 38 Ex. 95 Ref. 1-6 2-9 E1 3.81 3.09 0.137 0.080 49 Ex. 96
Ref. 1-6 2-9 F1 3.82 3.19 0.138 0.081 58 Ex. 97 H4 1-6 2-9 Ref.
3.85 6.05 0.138 0.081 112 Ex. 98 H4 1-6 2-9 E1 3.79 6.13 0.137
0.081 145 Ex. 99 H4 1-6 2-9 F1 3.80 6.31 0.137 0.082 174 Ex. 100 H3
1-6 2-9 Ref. 3.83 6.36 0.138 0.081 106 Ex. 101 H3 1-6 2-9 E1 3.79
6.41 0.138 0.079 136 Ex. 102 H3 1-6 2-9 F1 3.80 6.60 0.137 0.082
169
Comparative Example 55(Ref.55): Fabrication of OLED
[0308] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-8 (dopant) in Formula 2 and Compound 2-1 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples: 103-111 (Ex.103-111): Fabrication of OLEDs
[0309] An OLED where the EML includes the Compound 1-8 (dopant) in
Formula 2 and Compound 2-7 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.103-105), H4 in Formula 6 (Ex.106-108) or H3 in
Formula 6 (Ex.109-111), respectively, and the HBL includes the
Ref.HBL (Ex.103, 106 and 109), E1 in Formula 8 (Ex.104, 107 and
110) or F1 in Formula 10 (Ex.105, 108 and 111), respectively, were
fabricated.
Experimental Example 13: Measurement of Luminous Properties of
OLEDs
[0310] Luminous properties for each of the OLEDs fabricated in
Examples 103-111 and Comparative Example 55 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 13.
TABLE-US-00013 TABLE 13 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 55 Ref. 1-8 2-1 Ref.
3.92 3.12 0.136 0.081 28 Ex. 103 Ref. 1-8 2-7 Ref. 3.93 3.08 0.139
0.082 42 Ex. 104 Ref. 1-8 2-7 E1 3.87 3.17 0.137 0.081 50 Ex. 105
Ref. 1-8 2-7 F1 3.91 3.22 0.137 0.082 59 Ex. 106 H4 1-8 2-7 Ref.
3.92 6.17 0.138 0.081 119 Ex. 107 H4 1-8 2-7 E1 3.88 6.29 0.137
0.080 149 Ex. 108 H4 1-8 2-7 F1 3.89 6.44 0.137 0.081 175 Ex. 109
H3 1-8 2-7 Ref. 3.90 6.48 0.138 0.081 118 Ex. 110 H3 1-8 2-7 E1
3.88 6.67 0.138 0.081 142 Ex. 111 H3 1-8 2-7 F1 3.89 6.72 0.136
0.082 167
Comparative Example 56 (Ref.56): Fabrication of OLED
[0311] An OLED where the EBL includes the Ref.EBL, the EML includes
Compound 1-8 (dopant) in Formula 2 and Compound 2-3 (host) and the
HBL includes the Ref.HBL was fabricated.
Examples: 112-120 (Ex.112-120): Fabrication of OLEDs
[0312] An OLED where the EML includes the Compound 1-8 (dopant) in
Formula 2 and Compound 2-9 (host) in Formula 4, the EBL includes
the Ref.EBL (Ex.112-114), H4 in Formula 6 (Ex.115-117) or H3 in
Formula 6 (Ex.118-120), respectively, and the HBL includes the
Ref.HBL (Ex.112, 115 and 118), E1 in Formula 8 (Ex.113, 116 and
119) or F1 in Formula 10 (Ex.114, 117 and 120), respectively, were
fabricated.
Experimental Example 14: Measurement of Luminous Properties of
OLEDs
[0313] Luminous properties for each of the OLEDs fabricated in
Examples 112-120 and Comparative Example 56 were measured using the
same procedure as in Experimental Example 1. The measurement
results are indicated in the following Table 14.
TABLE-US-00014 TABLE 14 Luminous Properties of OLEDs Sample EBL D H
HBL V EQE (%) CIE(x) CIE(y) T.sub.95 (hr) Ref. 56 Ref. 1-8 2-3 Ref.
3.80 3.05 0.137 0.081 27 Ex. 112 Ref. 1-8 2-9 Ref. 3.81 3.07 0.138
0.083 36 Ex. 113 Ref. 1-8 2-9 E1 3.76 3.06 0.137 0.083 42 Ex. 114
Ref. 1-8 2-9 F1 3.80 3.18 0.137 0.083 52 Ex. 115 H4 1-8 2-9 Ref.
3.82 6.05 0.137 0.083 107 Ex. 116 H4 1-8 2-9 E1 3.78 6.12 0.136
0.084 132 Ex. 117 H4 1-8 2-9 F1 3.79 6.30 0.136 0.084 156 Ex. 118
H3 1-8 2-9 Ref. 3.84 6.38 0.137 0.083 102 Ex. 119 H3 1-8 2-9 E1
3.76 6.42 0.136 0.084 129 Ex. 120 H3 1-8 2-9 F1 3.81 6.62 0.136
0.083 144
[0314] Summarizing the results in Tables 7 to 14, compared to the
OLEDs fabricated in Ref.49 to Ref.56 where the EML includes a
non-deuterated anthracene-based compound (Compound 2-1 or Compound
2-3) as the host, the OLEDs fabricated in Ex.49 to Ex.120 where the
EML includes a deuterated anthracene-based compound (Compound 2-7
or Compound 2-9) as the host improved luminous efficiency and
luminous lifespan.
[0315] In addition, compared to the OLEDs fabricated in Ex.58-66,
76-84, 94-102 and 112-120 where the EML includes the Compound 2-9
as the host, the OLEDs fabricated in Ex.49-57, 67-75, 85-93 and
103-111 where the EML includes the Compound 2-7 as the host
improved their luminous efficiency and luminous lifespan. In other
words, when the anthracene-based compound, where a naphthyl moiety
(1-naphthyl) is linked directly to one side of an anthracene moiety
and other naphthyl moiety (2-naphthyl) is linked directly or via a
bridging group (linker) to the other side of the anthracene moiety
and is deuterated, are used as the host in the EML, the luminous
efficiency and the luminous lifespan of the OLEDs are further
increased.
[0316] Also, when the boron-based compound (Compound 1-6 or
Compound 1-8) having an asymmetric chemical structure was used as
the dopant in the EML, the luminous efficiency and the luminous
lifespan of the OLEDs are further improved. Particularly, when the
Compound 1-6 (R.sub.91 is alkyl (tert-butyl), each of R.sub.81 and
R.sub.82 is aryl (phenyl) substituted with alkyl (tert-butyl) in
Formula 1B), is used as the dopant in the EML, the luminous
efficiency and the luminous lifespan of the OLEDs are improved
significantly.
[0317] Moreover, when the HBL includes the azine-based compound of
Formula 8 or the benzimidazole-based compound of Formula 10, the
OLEDs showed very excellent luminous efficiency and luminous
lifespan. Also, when the HBL includes the amine-based compound of
Formula 6, the luminous efficiency and the luminous lifespan of the
OLED can be maximized.
[0318] In addition, when the EML includes the deuterated
anthracene-based compound (Compound 2-7 or Compound 2-9) and the
boron-based compound of Formula 1B, the EBL includes the
amine-based compound of Formula 5 and the HBL includes the
azine-based compound of Formula 7 or the benzimidazole-based
compound of Formula 9, the luminous efficiency and the luminous
lifespan of the OLED are remarkably improved.
[0319] It will be apparent to those skilled in the art that various
modifications and variations can be made in the organic light
emitting device of the present disclosure without departing from
the scope of the disclosure. Thus, it is intended that the present
disclosure cover the modifications and variations of the present
disclosure provided they come within the scope of the appended
claims.
* * * * *